Herbicidal oxatricyclic ethers

ABSTRACT

This invention relates to certain herbicidal oxatricyclic ethers, agriculturally suitable compositions thereof and a method for their use as broad spectrum preemergent or postemergent herbicides.

BACKGROUND OF THE INVENTION

This invention relates to certain herbicidal ethers, agriculturally suitable compositions thereof, and a method for their use as broad spectrum preemergent or postemergent herbicides.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

U.S. Pat. No. 4,670,041 discloses herbicidal compounds of the formula: ##STR1## wherein, inter alia: Y is (--CR⁵ R⁶ --)n in which n is 0, 1 or 2; and

R⁵ and R⁶ (in part) form an alkylene group containing 4 or 5 carbon atoms.

U.S. Pat. No. 4,828,603 discloses herbicidal compounds of the formula: ##STR2## wherein, inter alia: X is O, S, NR or CH₂ ; and

Y is (in part) CH₂.

SUMMARY OF THE INVENTION

Now new compounds effective for controlling the growth of undesired vegetation have been discovered. Accordingly, this invention is directed to compounds of Formulas I through VI including stereoisomers thereof, suitable compositions comprising said compounds and the use of said compounds or compositions as broad spectrum preemergent and postemergent herbicides ##STR3## wherein n is 2, 3 or 4;

m is 1, 2, 3 or 4;

p is 1 or 2;

R¹ is straight chain C₁ -C₃ alkyl;

R² is H, C₁ -C₄ alkyl, C_(2-C) ₄ alkenyl or C₂ -C₄ alkynyl;

R³ and R⁴ are independently H, C₁ -C₄ alkyl, C₂ -C₄ alkenyl, C₂ -C₄ alkynyl or C₁ -C₃ alkyl substituted with OCH₃ or OCH₂ CH₃ ;

R⁵ and R⁶ are independently H, OCH₃ or C₁ -C₂ alkyl;

Q is CH₂ W or ##STR4## q and r are independently 0, 1 or 2; R⁷ is H, halogen, C₁ -₃ alkyl, OR⁸, SR⁸ or CN;

R⁸ is C₁ -C₃ alkyl or C₁ -C₃ haloalkyl;

Z is CH₂, NR⁹, O, S or may be CH and taken to form a double bond with an adjacent carbon;

R⁹ is H or C₁ -C₃ alkyl;

W is phenyl optionally substituted with 1-3 substituents selected from halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, OH, CN, C₁ -C₃ haloalkyl, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₂ -C₄ alkenyl and C₂ -C₄ alkynyl; or W is a 5-, 6- or 7-membered heterocyclic ring containing 1-3 heteroatoms selected from 1-2 nitrogens, 1-2 oxygens and 1-2 sulfurs, each ring optionally substituted with 1-2 substituents selected from halogen, CH₃ and OCH₃ ;

provided that

1) the sum of q and r is 0-2; and

2) if the sum of q and r is O then Z is CH₂.

A representative exemplification of the aforementioned heterocycles includes but is not limited to pyrrole, furan, thiophene, tetrahydropyran, tetrahydrofuran, isoxazole, oxazole, pyrazole, imidazole, thiazole, pyridine and pyrazine;

In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl" or "alkylthio", includes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.

"Alkoxy", "alkenyl" and "alkynyl" includes straight chain or branched isomers, e.g. ethoxy, n-propyloxy, isopropyloxy, 1-propenyl, 2-propenyl and 3-propenyl.

"Halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

The compounds of the invention which are preferred for either their biological activity and/or ease of synthesis are:

1. Compound of Formulas I through VI wherein:

R⁵ and R⁶ are independently H or C₁ -C₂ alkyl;

Q is CH₂ W or ##STR5## W is phenyl optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃ ; or W is tetrahydropyran, tetrahydrofuran, thiophene, isoxazole, pyridine or pyrazine, each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃.

2. Compounds of Preferred 1 wherein: R² is H, C₁ -C₃ alkyl, C₂ -C₃ alkenyl or C₂ -C₃ alkynyl.

3. Compounds of Preferred 2 wherein:

R³ and R⁴ are independently H, C₁ -C₃ alkyl, C₃ -C₄ alkenyl or C₃ -C₄ alkynyl.

4. Compounds of Preferred 3 wherein the compounds are of Formulas I, III and V.

5. Compounds of Preferred 4 wherein:

Q is CH₂ W, Q-1, Q-3, Q-4, Q-6, Q-7, Q-8 or Q-15;

R⁵ and R⁶ are independently H;

W is phenyl optionally substituted with 1-2 substituents selected from F, Cl, Br and CH₃ ; tetrahydrofuran; thiophene optionally substituted with Cl or Br; or pyridine.

6. Compounds of Preferred 5 wherein:

m is 1;

R¹ is CH₃ or CH₂ CH₃ ;

R² is H, CH₃, CH₂ CH₃ or allyl;

R³ and R⁴ are H;

Q is CH₂ W.

Compounds of the invention which are specifically preferred for their biological activity and/or ease of synthesis are the compounds of Preferred 6 which are:

(1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-fluorophenyl)methoxy]-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]nonane;

(1α,2α,4α,5β,6α)-(+/--5-[(2-chlorophenyl)methoxy]-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]nonane; and

(1α,2α,4α,5β,6α)-(+/-)-5-[(2-fluorophenyl)methoxy]-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]nonane.

Compounds of Formulas I-VI that have the QO group syn with respect to the oxygen-containing bridge are usually more herbicidally active than the anti form. The present invention contemplates all the herbicidally active forms resulting from synthesis and for deliberately created mixtures.

The compositions of the invention suitable for controlling the growth of undesired vegetation comprise an effective amount of any of the compounds disclosed herein and at least one of the following: surfactant, solid diluent or liquid diluent.

Methods for controlling the growth of undesired vegetation are similarly considered to be within the scope of the invention. These methods comprise applying to the locus to be protected an effective amount of any of the compounds disclosed herein. Of particular importance is the method wherein the locus to be protected is rice, corn, soybeans or cereals.

DETAILED DESCRIPTION OF THE INVENTION

The compounds I-VI of the invention are prepared by treating the appropriately substituted oxatricycloalkanols Ia-VIa (which are compounds of Formula I-VI wherein Q is H) with a compound of the formula QX in which X is a halogen atom or a mesyloxy or a tosyloxy group or the like. This reaction is carried out, as shown in Scheme 1, in the presence of a strong base, such as an alkali metal hydride, in an inert solvent, such as ethers, aromatic hydrocarbons, dimethylformamide and the like. Suitable temperatures for the reaction are preferably from 20° C. to 100° C. The product ethers are recovered and isolated by conventional techniques. ##STR6##

The alkylating agents QX are prepared in the conventional manners known to those skilled in the art from the alcohols QOH.

The alcohols, QOH, are generally known in the art and are most conveniently prepared through metal hydride (e.g., sodium borohydride) reduction of the corresponding carbonyl compounds or the corresponding ketones which can be derived from Friedel-Crafts type cyclization of derivatives of phenylalkylcarboxylic acid, phenoxyalkylcarboxylic acids, benzyloxyalkylcarboxylic acids, phenylthioalkylcarboxylic acids, and benzylthioalkylcarboxylic acids. Details may be found in a) T. Laird in Comprehensive Organic Chemistry, D. Barton, W. D. Ollis ed., Vol. 1, pp. 1165-1168, Pergamon Press, New York (1979); b) M. H. Palmer and N. M. Scollick, J. Chem. Soc. C., (1968), 2833; c) C. E. Dolgliesck and Mann, J. Chem. Soc., (1945), 893; d) C. D. Hurd and S. Hayao, J. Am. Chem. Soc., (1954), 76, 4299 and 5056; and e) R. Lesser, Chem. Ber. (1923), 56, 1642.

Alternatively, the compounds of Formulas I-VI may be prepared by the coupling procedure described in Scheme 2, which is used in cases where the standard Williamson ether synthesis proves problematic. This procedure uses a Lewis acidic metal oxide wherein the metal can remove the halide ion by forming an insoluble precipitate. For example, silver (I) oxide can be used and the silver halide is the co-product. Alternative metal oxides that may be used are HgO, CaO, MgO. N,N-Dimethylformamide and ethereal solvents, such as diethyl ether, tetrahydrofuran, dioxane, or 1,2-dimethoxyethane are the preferred solvents. Other solvents likely to provide good yields include dipolar aprotic solvents like dimethyl sulfoxide, acetone, and N,N'-dimethylpropyleneurea. ##STR7##

The oxatricycloalkanols Ia-VIa can be obtained generally by one or more of the following routes: directly by a) epoxidation-cyclization of unsaturated cyclic alcohols, with or without isolation of the epoxyalcohol intermediates; indirectly by b) Diels-Alder reactions of furans with dienophiles; or by c) Diels-Alder reactions of other dienes with dienophiles.

Non-limiting illustrations of the preparation of representative compounds follow.

Some of the compounds of Formula I can be prepared through the sequence shown in Scheme 3. Cyclohexene 1 can be prepared by methods known in the art or by modifications thereof (for example see Millward, J. Chem. Soc. 26 (1960)). Treatment of (1) with (2) yields the cyclohexenol (3). Treatment of (3) with peroxide and acid, as taught in U.S. Pat. No. 4,486,219 yields alcohol (4). Reaction of (4) with a reducing agent, such as lithium aluminum hydride, followed by treatment with a base, such as triethylamine, and toluenesulfonyl chloride at ambient temperature to 100° C. produces the corresponding monotosylate. Oxidation of the alcohol yields ketone (5). Treatment of (5) with a strong base, such as lithium diisopropylamide, followed by reduction of the ketone with a reducing agent, such as sodium borohydride, produces Ia. ##STR8##

Alternatively, compounds of Formula I can be prepared through the sequence shown in Scheme 4. Cyclohexenone (1) can be converted to hydroxy ester (6) by treatment with hydrogen cyanide, following by hydrochloric acid in methanol using the procedure of Hook, Mander and Urech, J. Org. Chem., 49, 3250 (1984) or modifications thereof. Treatment of alcohol (6) with peracid and acid as described in Scheme 3 yields the bicyclic alcohol (7). Treatment of the ester with a reducing agent, such as lithium aluminum hydride or a Grignard reagent (e.g., R⁵ M), followed by tosylation and oxidation of the alcohol yields bicyclic ketone (8). Treatment of (8) with strong base, such as lithium diisopropylamide, followed by reduction of the ketone yields alcohol Ia. ##STR9##

Compounds of Structure IIa can be prepared through the sequence shown in Scheme 5, or by modifications thereof. Compound (9) can be prepared by methods known in the art (for example see Veselovsky, Gybin, Lozanova, Moiseenkov, Smit and Caple, Tet. Lett., 175 (1988)). Alcohol IIa can be prepared from (9) using the sequence of reactions described in Scheme 3 or by modifications thereof.

Alternatively, compounds of Structure IIa can be prepared through the sequence shown in Scheme 6. Compound IIa can be prepared from (9) using the sequence of reactions described in Scheme 4 or by modifications thereof.

Compounds of Structure IIIa can be prepared by the sequence shown in Scheme 7. Diels-Alder reaction of (16) and (17) yields cyclohexene (18) (where X=halogen, tosylate or the like and m=1-4). Addition of a Grignard reagent (e.g., R³ M) or a reducing agent followed by treatment with peracid and acid as described in Scheme 4 gives alcohol (19). Oxidation of the alcohol to the ketone, followed by treatment with a strong base, such as lithium diisopropyl amide and subsequent reduction of the ketone yields IIIa. ##STR10##

Compounds of Structure IVa can be prepared using the sequence shown in Scheme 8. Compound (20) can be prepared by methods known in the art (for example see Buchi and Powell, J. Amer. Chem. Soc., 3126 (1970)). Conversion of (20) to IVa can be accomplished using the sequence of reactions described in Scheme 3 or by modifications thereof.

Compounds of Structure IVa can also be prepared using the sequence shown in Scheme 9 and described in Scheme 4.

Compounds of Structure Va can be prepared using the sequence shown in Scheme 10. Diels-Alder reaction of (25) and (26) yields cyclohexene (27), where X=halogen, tosylate or the like. Alcohol Va can be prepared from (27) using reactions like those described in Scheme 7 or by modifications thereof.

Alternatively, compounds of Structure Va can be prepared using the sequence shown in Scheme 11. Diels-Alder adduct (29) can be reduced with a reducing agent such as lithium aluminum hydride or reacted with a Grignard reagent (e.g., R³ M). The resulting alcohol can be treated with peracid under acidic conditions to generate the bicyclic dialcohol. Tosylation of the primary alcohol and oxidation of the secondary alcohol yields (30). Treatment with a strong base, such as lithium diisopropyl amide, and subsequent reduction of the ketone yields Va.

Compounds of Structure VIa can be prepared using the sequence shown in Scheme 12. Ketone (31) can be prepared by methods known in the art (for example see Buchi and Powell, J. Amer. Chem. Soc., 92, 3126 (1970)). Alkylation of (31) with a suitable electrophile (X=halogen, tosylate or the like) yields (32). Alcohol VIa can be prepared from (32) using the sequence of reactions described in Scheme 7 or by modifications thereof. ##STR11##

The following examples further illustrate the invention:

EXAMPLE 1 (1α,2α,4α,5β,6α)-(+/-)-5-((2,6,-difluorophenyl)methoxy)-6-methyl-7-oxatricyclo[4.2.1.²,4 ]nonane Step A: (±)-4-Methyl-4-cyclohexene-1,2-dicarboxylic anhydride

To 50 ml (0.50 mol) of isoprene was added 25 g (0.26 mol) of maleic anhydride portionwise with cooling. The reaction mixture was stirred at ambient temperature for four hours. The excess isoprene was removed under vacuum to give 40.5 g of a white solid, m.p. 63°-65° C.

NMR (CDC₁₃): δ 5.70 (br s,1H , 3.45 (m,2H), 2.50 (m,4H), 1.81 (s,3H).

IR (KBr): 2900, 1840, 1770, 1445, 1235, 965, 920, 800 cm⁻¹.

Step B: (±)-Cis-4-methyl-4-cyclohexene-1,2-dimethanol

To 300 ml of tetrahydrofuran at 0° C. was added 16.0 g (0.42 mol) lithium aluminum hydride portionwise keeping the reaction temperature between 0° C. and 5° C. A solution of 33.0 g (0.20 mol) of 4-methyl-4-cyclohexene-2,3-dicarboxylic anhydride in 100 ml of tetrahydrofuran was added dropwise over 2 hours keeping the temperature between 0° C. and 10° C. The reaction mixture was warmed to ambient temperature and stirred for 2 hours. The reaction was cooled to 0° C. and 35 ml of ethyl acetate was added dropwise, followed by dropwise addition of 35 ml isoropanol and 35 ml water. The reaction mixture was filtered through celite using acetone, dried with MgSO₄, filtered, and concentrated to 33.0 g of oil. Flash chromatography in 3:1 hexanes-ethylacetate, followed by 1:1 hexanes-ethylacetate and finally ethylacetate alone yielded 18.2 g of oil.

NMR (CDCl₃): δ 5.35 (br s,1H), 3.68 (m,2H), 3.60 (m,2H), 3.10 (br s,2H) ,2.05 (br s,6H), 1.64 (s,3H).

IR (neat): 3500-3100, 1730w, 1440, 1010 cm⁻¹.

MS (CI): 157 (M+1), 139,121.

Step C: 2-endo,4-exo-(±)-4-hydroxy55-methyl-6-oxabicyclo[3.2.1]octane-2-methanol

To a suspension of 39.0 g (0.124 mol) of 55% m-chloroperbenzoic acid in 400 ml of methylene-chloride at 0° C. was added 19.4 g (0.124 mol) of (±)-cis-4-methyl-1,4-cyclohexene-1,2-dimethanol in 100 ml of methylene chloride over 15 minutes keeping the temperature less than 8° C. The reaction mixture was warmed to ambient temperature and stirred for 24 hours. The reaction was cooled to 0° C. and 30 ml of a saturated aqueous solution of Na₂ S₂ O₃ was added dropwise keeping the temperature less than 8° C. The reaction mixture was dried with MgSO₄, filtered, and concentrated under reduced pressure. Flash chromatography in 3:1 hexanes-ethylacetate, 1:1 hexanes-ethylacetate, then ethylacetate alone yielded 6.1 g oily solid.

NMR (CDCl₃): δ 3.80 (br d,2H), 3.60 (br d,1H), 3.45 (d,2H), 2.70 (br s,2H), 2.42 (br s,1H), 2.0 (m), 1.5 (m), 1.33 (s,3H).

IR (neat): 3400-3200, 2900, 1450, 1380, 1060, 1000, 820 cm⁻¹.

MS (CI): 173 (M+1), 213,155.

Step D: 2-endo,4-exo-(+/-)-[4-hydroxy-5-methyl-6-oxyabicyclo[3.2.1]-octan-2-yl)methyl 4-methylbenzenesulfonate

To 14.9 g (0.086 mol) of 2-endo-4-exo-(±)-4-hydroxy-5-methyl-6-oxabicyclo[3.2.1]octane-2-methanol in 25 ml of pyridine at 0° C. was added 18.06 g (0.095 mol) of p-toluene-sulfonylchloride portionwise keeping the temperature less than 5° C. The reaction was stirred at 0° C. for 10 minutes, then 0.97 g (0.008 mol) 4-dimethylaminopyridine was added. The reaction was warmed to ambient temperature and stirred for 6 hours. An additional 9.00 g of p-toluenesulfonyl chloride and 1.00 g of 4-dimethylamino pyridine were added and the reaction mixture was stirred for 72 hours. To the reaction was added 20 ml water. The mixture was extracted twice with ether and then twice with methylene chloride. The combined organic layers were dried, filtered, and concentrated under reduced pressure. Flash chromatography using 3:1 hexanes-ethylacetate, then 1:1 hexanes-ethylacetate yielded 21.03 g of white solid, m.p. 87°-89° C.

NMR (CDCl₃): δ 7.75 d(2H), 7.38 d(2H), 3.83 d(2H), 3.6 m(3H), 2.46 s(3H), 2.38 m(1H), 2.21 m(1H), 1.5 m, 1.30 s(3H).

IR (neat): 3440 br, 2950, 2900, 1609, 1459, 1360, 1190, 1180, 1070, 1050, 960, 830, 820, 680 cm⁻¹.

MS (CI): 327 (m+1), 344, 309.

Step E: 2-endo-(+/-)-5-methyl-2-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-6-oxabicyclo[3.2.1]-octan-4-one

To 64.5 ml (0.13 mol) of 2M oxalyl chloride in methylene chloride at -78° C. was added dropwise 13.7 ml (0.19 mol) dimethyl sulfoxide in 20 ml methylene chloride. The reaction was stirred for 10 minutes, then 21.03 g (0.06 mol) of 2-endo,4-exo(+/-)-[4-hydroxy-5-methyl-6-oxabicyclo[3.2.1]-octan-2-yl]methyl 4-methyl benzenesulfonate in 50 ml methylene chloride was added dropwise to the reaction mixture. The reaction was stirred at -78° C. for 45 minutes, then 40.5 ml (0.29 mol) of triethylamine in 40 ml of methylene chloride was added dropwise. The reaction mixture was warmed to ambient temperature and stirred for 20 hours. To the reaction was added 50 ml water. The reaction was extracted with methylene chloride. The organic layer was washed with water, dried over MgSO₄, filtered, and concentrated under reduced pressure. Flash chromatography in 3:1 hexanes-ethylacetate, followed by 1:1 hexanes-ethylacetate yielded 19.49 g of white solid, m.p. 104°-106° C.

NMR (CDCl₃): δ 7.80 d(2H), 7.37 d(2H), 3.95 m(4H), 2.62 m(1H), 2.47 s(3H), 2.4-2.0 m, 1.80 d(1H), 1.32 s(3H).

IR (neat): 2950 br, 1730, 1605, 1365, 1190, 1102, 970, 950, 840, 810, 670, 560, 525 cm⁻¹.

MS (CI): 342 (M+NH₄ ⁺).

Step F: 1α,2α,4α,6α)-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]nonan-5one

To 2.38 ml (0.017 mol) diisopropylamine in 10 ml tetrahydrofuran at -78° C. was added dropwise 6.17 ml (0.015 mol) 2.5M butyllithium in hexanes. The reaction mixture was warmed in -20° C. and then cooled back to -78° C. To this solution was added dropwise 5.0 g (0.015 mol) 2-endo-(+/-)-5-methyl-2-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-6-oxabicyclo[3.2.1]-octan-4-one in 10 ml tetrahydrofuran. The reaction mixture was allowed to warm to ambient temperature and stirred for four hours. The reaction was cooled to 0° C. and 50 ml of isopropanol was added. Ether was added and organic layer was washed with water, dried over MgSO₄, filtered, and concentrated to an oil. Flash chromatography in 20:1 hexanes:ethylacetate, followed by 6:1 hexanes:ethylacetate yielded 1.32 g of oil.

¹ H NMR (CDCl₃): δ 3.78 (dd,1H), 3.71 (d,1H), 2.8 (dd,1H), 2.0 (m,3H), 1.60 (ddd,1H), 1.44 (dd,1H), 1.11 ddd(1H), 1.32 s 3H.

¹³ C NMR (CDCl₃): δ 18.47 (CH₃), 15.14 (CH₂), 46.59 (CH₂), 71.76 (CH₂), 21.15 (CH), 25.14 (CH), 34.24 (CH), 84.58 (C), 206.91 (C═O).

IR (neat): 3000-2860, 1695 (s), 1440, 1335, 1260, 1150, 1105, 1010, 972, 810 cm⁻¹.

GCMS: 152 (M.⁺).

Step G: (1α,2α,4α,5β,6α)-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]non-5-ol

To 1.21 g (0 0080 mol) of (1α,2α,4α,6α)-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]nonan-5-one in 10 ml tetrahydrofuran at -78° C. was added 8.76 ml (0.0088 mol) of 1M Super Hydride®. The reaction mixture was warmed to ambient temperature, then cooled to -78° C. An additional 4.0 ml (0.004 mol) of 1M Super Hydride® was added. The reaction mixture was warmed to 0° C. and quenched with 20 ml of water. The reaction mixture was extracted twice with ether and twice with methylene chloride. The combined organic layers were dried over MgSO₄, filtered and concentrated. Flash chromatography in 6:1 hexanes:ethylacetate, followed by 3:1 hexanes:ethylacetate yielded 1 16 g oil.

NMR (CDCl₃): δ 4.4 (brs,1H), 3.78 (dd,1H), 3.60 (dd,1H), 3.48 (d,1H), 2.60 (m,1H), 2.00 (d,1H), 1.6 (m,2H), 1.33 (s,3H), 1.20 (m,1H), 0.9 (m,1H), 0.55 (m,1H).

IR (neat): 3400 (br), 3000-2860, 1350, 1230, 1060, 1010, 962, 795 cm⁻¹.

GCMS: 154 (M.⁺).

Step H: (1α,2α,4α,5β,6α)-(+/-)-5-((2,6-difluorophenyl)methoxy))-6-methyl-7-oxatricyclo-[4.2.1.0⁴,2 ]-nonane

To 0.06 g (0.0016 mol) hexane-washed 60% sodium hydride was added 20 ml tetrahydrofuran at 0° C. To this suspension was added 0.20 g (0.0013 mol) (1α,2α,4α,5β,6α)-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]-non-5-ol in tetrahydrofuran. After 10 minutes, 0.32 g (0.0016 mol) 2-fluorobenzylbromide was added. The reaction mixture was stirred for 24 hours at ambient temperature, then 20 ml water was added. The reaction mixture was extracted twice with ether and twice with methylene chloride. The combined organic layers were dried over MgSO₄, filtered, and concentrated. Flash chromatography in 6:1 hexanes:ethylacetate yielded 0.22 g of oil.

¹ H NMR (CDCl₃): δ 7.22 (m,1H), 6.85 (dd,2H), 4.89 (d,1H), 4.67 (d,1H), 3.59 (dd,1H), 3.50 (d,2H), 2.59 (m,1H), 1.61 (dq,1H), 1.50 (d,2H), 1.23 (s,3H), 1.16 (m,1H), 0.89 (q,1H), 0.59 (dt,1H).

¹³ CNMR (CDCl₃): δ 23.06 (CH₃), 7.21 (CH₂), 41.93 (CH₂), 56.92 (CH₂), 70.78 (CH₂), 11.02 (CH), 22.22 (CH), 34.05 (CH), 79.40 (CH), 111.1 (CH), 129 7 (CH), 81.09 (C), 161.05 (C), 163,57 (C).

MS(DCI/NH₃): 282 (M+H⁺), 299 (M+NH₄ ⁺), 137.

EXAMPLE 2 (1α,2α,5α,6α)-(+/-)-5-((2-chloro-6-fluorophenyl)-methoxy))-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]-nonane

To 0.1 g (2.1 mmol) of hexane-washed 60% sodium hydride in tetrahydrofuran was added 0.3 g (2.0 mmol) of (1α,2α,5α,5β,6α)-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]-nonan-5-ol. After 10 minutes, 0.26 ml (2.1 mmol) of 2-chloro-6-fluorobenzyl bromide was added. The reaction mixture was heated 70° C. When the reaction was complete water was added and the reaction mixture was extracted twice with ether. The combined organic extracts were dried over MgSO₄, filtered, and concentrated. Flash chromatography in 20:1 hexanes:ethylacetate yielded 0.26 g solid, m.p. 69°-71° C.

¹ H NMR (CDCl₃): δ 7.2 (m,2H), 6.99 (m,1H), 4.95 (d,1H), 4.72 (d,1H), 3.6 (dd,1H), 3.5 (d,2H), 2.60 (m,1H),1.6 (m,1H), 1.49 (dd,2H),1.25 (s,3H), 1.20 (m,1H), 0.90 (m, 1H), 0.60 (m, 1H).

¹³ CNMR (CDCl₃): δ 23.1 (CH₃), 7.2 (CH₂), 42.9 (CH₂), 60.0 (CH₂), 70.7 (CH₂), 11.0 (CH), 22.1 (CH), 34 (CH), 79.4 (CH), 113.8 (CH), 125.2 (CH), 129.7 (CH), 81.0 (C), 124.1 (C), 129.4 (C), 136.8 (C), 162 (C).

MS(DCI/NH₃): 297 (MH⁺), 299 (MH⁺), 314 (MNH₄ ⁺), 316 (MNH₄ ⁺).

EXAMPLE 3 (1α,2α,5β,6α)-(+/-)-5-((2-chloro-6-fluorophenyl)methoxy)-6-ethyl-7-oxatricyclo[4.2.1.0²,4 ]nonane Step A: (±)-4-Ethyl-4-cyclohexene-1,2-dicarboxylic anhydride

Maleic anhydride (19.6 g, 0.2 mol) and 20 g (0.24 mol) 2-ethyl-1,3-butadiene were stirred at ambient temperature for 24 hours. The excess 2-ethyl-1,3-butadiene was removed in vacuo to yield 36 g of white solid, m.p. 65°-67° C.

IR (KBr): 2980-2860, 1835, 1770, 1235, 980, 930 cm⁻¹.

Step B: 2-endo,4-exo-(+/-)-4-hydroxy-5-ethyl-6-oxabicyclo-[3.2.1]octane-2-methanol

To 16 g (0.42 mol) lithium aluminum hydride in 200 ml tetrahydrofuran at 0° C., was added 33.0 g (0.2 mol) (+/-)-4-ethyl-4-cyclohexene-1,2-dicarboxylic anhydride dropwise over 45 minutes keeping the temperature less than 5° C. The reaction was warmed to ambient temperature and stirred for 24 hours. The reaction was quenched at 0° C. by sequential addition of ethyl acetate, isopropanol, and water. The mixture was filtered through celite with acetone, dried over MgSO₄, filtered, and concentrated under reduced pressure. The resulting oil was dissolved in methylene chloride and cooled to 0° C. A solution of 33.6 g (0.11 mol) m-chloroperbenzoic acid was added keeping the temperature less than 5° C. The reaction was warmed to ambient temperature and stirred for 72 hours. A solution of saturated sodium thiosulfate was added, the mixture was dried over MgSO₄, filtered, and concentrated under reduced pressure. Flash chromatography in 3:1 hexanes-ethylacetate, followed by 1:1 hexanes-ethylacetate, followed by ethylacetate yielded 11.60 g of product.

NMR (CDCl₃): δ 3.8 m(4H), 3.48 d(2H), 2.42 br t(1H), 2.2-1.5 m, 0.94 t(3H).

Step C: 2-endo,4-exo(+/-)-[4-hydroxy-5-ethyl-6-oxabicyclo-[3.2.1]octan-2-yl]methyl 4-methylenebenzene sulfonate

To 11.06 g (0.06 mol) of 2-endo,4-exo-(+/-)-4-hydroxy-5-ethyl-6-oxabicyclo[3.2.1]octane-2-methanol in pyridine at 0° C. was added 13.6 9 (0.07 mol) p-toluene-sulfonyl chloride portionwise. The reaction was stirred for 10 minutes, then a catalytic amount of dimethylaminopyridine was added. The reaction was stirred for 24 hours. Ether was added, and the reaction was washed sequentially with water, 10% HCl, and water, then dried over MgSO₄, filtered, and concentrated under reduced pressure. Flash chromatography in 3:1 hexanes-ethylacetate, then 1:1 hexane-ethylacetate yielded 10.5 g of product.

NMR (CDCl₃): δ 7.76 d(2H), 7.33 d(2H), 3.83 d(2H), 3.63 m(3H), 2.3 m(2H), 2.45 s(3H), 1.98 d(1H), 1.7-1.4 m, 0.91 t(3H).

Step D: (2-endo-5-ethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-6-oxabicyclo[3.2.1]octan-4-one

Swern oxidation (using the conditions described in Example 1, Step E), with 5.87 g (0.017 mol) of 2-endo,4-exo-(+/-)-[4-hydroxy-5-ethyl-6-oxabicyclo[3.2.1]octan-2-yl]methyl 4-methylbenzene sulfonate, 17.4 ml (0.035 mol) of 2M oxalylchloride in methylene chloride, 3.7 ml (0.052 mol) dimethylsulfoxide, and 10.9 ml (0.078 mol) triethylamine yielded 7.17 g.

NMR (CDCl₃): δ 7.78 (d,2H), 7.37 (d,2H), 3.92 (m,4H), 2.62 (m,1H), 2.47 (s,3H), 2.3 (m,3H), 2.20 (dd,1H), 1.7 (m,2H), I.61 (d,1H), 0.91 (t,3H).

Step E: (1α,2α,4α,5β,6α)-6-ethyl-7-oxatricyclo[4.2.1.0²,4 ]-non-5-ol

Treatment with lithium diisopropylamine (using the conditions described in Example 1, Step F) with 6.0 g (0.018 mol) of (2-endo)-5-ethyl-2-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-6-oxabicyclo[3.2.1]octan-4-one, 2.74 ml (0.02 mol) diisopropylamine, and 7.1 ml (0.018 mol) 2.5 M butyllithium in hexanes gave 1.65 g of the tricyclic ketone.

NMR (CDCl₃): δ 3.74 (s,2H), 2.8 (d,1H), 2.0 (m,3H), I.78 (q,1H), 1.60 (m,1H), 1.42 (q,1H), 1.10 (m,1H), 0.90 (t,3H).

Treatment of the above compound with Super Hydride® (13.6 ml, 0.014 mol) as described in Example 1, Step G gave 1.73 g oil.

NMR (CDCl₃): δ 3.83 (dd,1H), 3.55 (dd,1H), 3.54 (d,1H), 2.6Q (m,1H), 1.92 (d,1H), 1.8-1.5 (m,3H), 1.40 (d,1H), 1.22 (m,1H), 0.96 (m,1H), 0.86 (t,3H), 0.61 (q,1H).

Step F: (1α,2α,5β,6α)-(+/-)-5-((2-chloro-6-fluorophenyl)methoxy))-6-ethyl-7-oxatricyclo[4.2.1.0⁴,2 ]-nonane

(1α,2α,5β,6α)-6-ethyl-7-oxatricyclo[4.2.1.0²,4 ]-nonan-5-ol (0.2 g, 0.0011 mol) was treated with 0.05 g (0.0013 mol) 60% sodium hydride and 0.16 ml (0.0013 mol) 2-chloro-6-fluorobenzylbromide using the conditions described in Example 2 to give 0.22 g white solid, m.p. 73°-75° C.

NMR (CDCl₃): δ 7.18 (m,2H), 6.98 (m,1H), 4.91 (d,1H), 4.81 (d,1H), 3.59 (d,1H), 3.53 (m,2H), 2.59 (m,1H), 1.7-1.4 (m,4H), 1.3 (d,1H), 1.21 (m,1H), 0.91 (m,1H), 0.65 (t,3H), 0.64 (m,1H).

IR (KBr): 2950, 2850, 1600, 1572, 1450, 1072, 980, 770 cm⁻¹.

MS: 281 (M⁺ -Et), 143.

Utilizing the above disclosure the following compounds can be prepared:

                                      TABLE 1                                      __________________________________________________________________________      ##STR12##                                                                     m    Q                         m    Q                                          __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.5 R.sup.6 H                                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-CHCH.sub.2)C.sub.6 H.sub.4                                                                   4    CH.sub.2 (2-CHCH.sub.2)C.sub.6                                                 H.sub.4                                    R.sup.1 CH.sub.3, R.sup.5 R.sup.6 CH.sub.3                                     1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (w,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.3 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.3 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        R.sup.1 CH.sub.3, R.sup.5 OCH.sub.3, R.sup.6 H                                 1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub. 5)                1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub. 6 H.sub.5)                2    CH.sub.2 (2-FC.sub.3 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.3 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        R.sup.1  CH.sub.3, R.sup.5 OCH.sub.3, R.sup.6 CH.sub.3                         1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 )C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.3 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.3 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub. 2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        R.sup.1 CH.sub.2 CH.sub.3, R.sup.5 R.sup.6 H                                   1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.3 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.3 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR13##                                                                     R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                            n    Q                         n    Q                                          __________________________________________________________________________     2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-pyridyl)      3    CH.sub.2 (2-pyridyl)                       2    CH.sub.2 (2-thienyl)      3    CH.sub.2 (2-thienyl)                       2    CH.sub.2 -(2-furanyl)     3    CH.sub.2 -(2-furanyl)                      2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             2    Q-1                       3    Q-1                                        2    Q-3                       3    Q-3                                        2    Q-4                       3    Q-4                                        2    Q-6                       3    Q-6                                        2    Q-7                       3    Q-7                                        2    Q-8                       3    Q-8                                        2    Q-15                      3    Q-15                                       __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                            n    Q                         n    Q                                          __________________________________________________________________________     2    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           2    CH.sub.2 (2-(CF.sub.3 )C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   4    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 4    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              4    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   4    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         4    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             4    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   4    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       4    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       4    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       4    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             4    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             4    Q-1                       2    Q-1                                        4    Q-3                       2    Q-3                                        4    Q-4                       2    Q-4                                        4    Q-6                       2    Q-6                                        4    Q-7                       2    Q-7                                        4    Q-8                       2    Q-8                                        __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                                                           R.sup.1 R.sup.2 CH.sub.3, R.sup.3 R.sup.5                                      R.sup.6 H                                       n    Q                         n    Q                                          __________________________________________________________________________     4    Q-15                      2    Q-15                                       4    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           4    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   4    CH.sub.2 (2-CHCH.sub. 2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-CHCH.sub.2)C.sub.6                                                 H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                            m    Q                         m    Q                                          __________________________________________________________________________     3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    __________________________________________________________________________     R.sup.1 R.sup.3 CH.sub.3, R.sup.2 R.sup.5 R.sup.6 H                            n     Q                        n    Q                                          __________________________________________________________________________     2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub. 6                                               H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________     R.sup.1 R.sup.5 CH.sub.3, R.sup.2 R.sup.3 R.sup.6 H                            n    Q                         n    Q                                          __________________________________________________________________________     2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4 )                                                                          4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________     R.sup.5 R.sup.1 CH.sub.3, R.sup.2 R.sup.3 H, R.sup.6 OCH.sub.3                 n    Q                         n    Q                                          __________________________________________________________________________     2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub. 2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.6  H, R.sup.5 OCH.sub.3                n    Q                         n    Q                                          __________________________________________________________________________     2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub. 4)                                                                4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR14##                                                                     m    Q                         m    Q                                          __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.3 R.sup.4 R.sup.5 R.sup.6 H                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  1    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   1    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CF.sub.3 (C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    R.sup.1 CH.sub.3 R.sup.3 R.sup.4, R.sup.5 R.sup.6 H                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3 )                                                                  2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3 (C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(CF.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CF.sub.3 (C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    R.sup.1 CH.sub.3, R.sup.3 R.sup.4 CH.sub.2 CH.sub.3, R.sup.5 R.sup.6 H         1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3 (C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(CF.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub. 6 H.sub.4)                                                                          4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub. 3)                                                                  4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CF.sub.3 (C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    R.sup.1 R.sup.5 CH.sub.3, R.sup.3 R.sup.4 R.sup.6 H                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub. 3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   R.sup.1 R.sup.5 CH.sub.3, R.sup.3 R.sup.4 H, R.sup.6 OCH.sub.3                 1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub. 6 H.sub.3)                                                                 3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub. 2 C.sub.6 H.sub.3)                                                                 4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   R.sup.1 R.sup.4 CH.sub.3, R.sup.3 R.sup.5 R.sup.6 H                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub. 2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       3    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub. 2 (2,6-F.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       4    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR15##                                                                     P    Q                         P    Q                                          __________________________________________________________________________     R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4 )            1    CH.sub.2 (2,6-BrC.sub.6 H.sub.3)                                                                         2    CH.sub.2 (2,6-BrC.sub.6 H.sub.3)           1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub. 4                                   R.sup.1 CH.sub.2 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 R.sup.6 H                   1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-BrC.sub.6 H.sub.3)                                                                         2    CH.sub.2 (2,6-BrC.sub.6 H.sub.3)           1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    R.sup.3 R.sup.5 R.sup.6 H, R.sup.1 R.sup.2 CH.sub.3                                                           R.sup.1 R.sup.3 CH.sub.3, R.sup.2 R.sup.5                                      R.sup.6 H                                       1    CH.sub.2 (C.sub. 6 H.sub.5)                                                                              1    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            1    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   1    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           1    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           1    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           1    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           1    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   R.sup.5 R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.6 H                                                           R.sup.1 R.sup.5 CH.sub.3, R.sup.2 R.sup.3                                      H, R.sup.6 OCH.sub.3                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               1    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            1    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   1    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           1    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           1    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           1    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           1    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   1    Q-1                       1    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)         2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub. 2 (2-tetrahydropyranyl)                                                                          2    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5 H, R.sup.6 OCH.sub.3                                                R.sup.1 CH.sub.3, R.sup.2 R.sup.3 R.sup.5                                      H, R.sup.6 OCH.sub.3                            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl,6-FC.sub.6 H.sub.3)                                                                       2    CH.sub.2 (2-Cl,6-FC.sub. 6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________      ##STR16##                                                                     m    Q                         m    Q                                          __________________________________________________________________________          R.sup.1 = CH.sub.3, R.sup.3 = R.sup.4 = H,                                                                    R.sup.1 = CH.sub.3, R.sup.3 = R.sup.4                                          = H,                                            R.sup.5 = R.sup.6 = H          R.sup.5 = R.sup.6 = H                      1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (CH.sub.6 H.sub.5)                1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub. 6 H.sub.3)                                                                 2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub. 6 H.sub.4)                                                                        2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub. 6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                         R.sup.1 = CH.sub.2 CH.sub.3 ,  R.sup.1 = CH.sub.2 CH.sub.3,                    R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                                                                     R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6                                          = H                                        1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub. 2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       1    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       1    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             1    Q-1                       2    Q-1                                        1    Q-3                       2    Q-3                                        1    Q-4                       2    Q-4                                        1    Q-6                       2    Q-6                                        1    Q-7                       2    Q-7                                        1    Q-8                       2    Q-8                                        1    Q-15                      2    Q-15                                       1    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           1    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   1    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub. 2 (2-FC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        3    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                         R.sup.1 = R.sup.5 = R.sup.6 = CH.sub.3                                                                        R.sup.1 = R.sup.5 = R.sup.6 =                                                  CH.sub.3                                        R.sup.3 = R.sup.4 = H          R.sup.3 = R.sup.4 = H                      1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub. 6 H.sub.4)                                                                           3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                        R.sup.1  = R.sup.2 = CH.sub.3, R.sup.1 = R.sup.2 = CH.sub.3,                   R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                                                                     R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6                                          = H                                        1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub. 6 H.sub.4)                                                                 4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                        R.sup.1 =R.sup.5 = CH.sub.3,   R.sup.1 =R.sup.5 = CH.sub.3,                    R.sup.3 = R.sup.4 = R.sup.6 = H                                                                               R.sup.3 = R.sup.4 = R.sup.6 = H            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub. 6 H.sub.4)                                                                          4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrhydrofuranyl)                                                                            4    CH.sub.2 (2-tetrhydrofuranyl)              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                        R.sup.1 =CH.sub.3, R.sup.2 = OCH.sub.3,                                                                       R.sup.1 = CH.sub.3, R.sup.5 =                                                  OCH.sub.3,                                      R.sup.3 = R.sup.4 = R.sup.6 =  H                                                                              R.sup.3 = R.sup.4 = R.sup.6 = H            1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrhydrofuranyl)                                                                            4    CH.sub.2 (2-tetrhydrofuranyl)              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3                                          )                                          2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                        R.sup.1 = R.sup.6 = CH.sub.3, R.sup.5 =                                                                       R.sup.1 = R.sup.6 = CH.sub.3, R.sup.5                                          =                                               OCH.sub.3, R.sup.3 = R.sup.4 = H                                                                              OCH.sub.3, R.sup.3 = R.sup.4 = H           1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                        R.sup.1 = R.sup.3 = R.sup.4 = CH.sub.3,                                                                       R.sup.1 = R.sup.3 = R.sup.4 =                                                  CH.sub.3,                                       R.sup.5 = R.sup.6 = H          R.sup.5 = R.sup.6 = H                      1    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 1    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              1    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             1    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   1    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        1    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             1    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   1    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             1    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             1    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   1    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                3    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   1    Q-1                       3    Q-1                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4 )                                                                           4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2-(CH.sub.3 (C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CH.sub.3 (C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6 H.sub.4)                                                                4    CH.sub.2 (2-(CHCH.sub.2 (C.sub.6                                               H.sub.4)                                   __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR17##                                                                     n    Q                         n    Q                                          __________________________________________________________________________          R.sup.1 = CH.sub.3,            R.sup.1 = CH.sub.3,                             R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                                                                     R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6                                          = H                                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-pyridyl)      3    CH.sub.2 (2-pyridyl)                       2    CH.sub.2 (2-thienyl)      3    CH.sub.2 (2-thienyl)                       2    CH.sub.2 (2-furanyl)      3    CH.sub.2 (2-furanyl)                       2    CH.sub.2 (2-tetrahydrofuranyl)                                                                           3    CH.sub.2 (2-tetrahydrofuranyl)             2    CH.sub.2 (2-tetrahydropyranyl)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             2    Q-1                       3    Q-1                                        2    Q-3                       3    Q-3                                        2    Q-4                       3    Q-4                                        2    Q-6                       3    Q-6                                        2    Q-7                       3    Q-7                                        2    Q-8                       3    Q-8                                        2    Q-15                      3    Q-15                                            R.sup.1 = CH.sub.3,            R.sup.1 = CH.sub.3,                             R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                                                                     R.sup.3 =  R.sup.4 = R.sup.5 =                                                 R.sup.6 = H                                2    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  3    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           2    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   3    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                         R.sup.1 = CH.sub.2 CH.sub.3,   R.sup.1 = CH.sub.2 CH.sub.3,                    R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                                                                     R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6                                          = H                                        4    CH.sub.2 (C.sub.6 H.sub.5)                                                                               2    CH.sub.2 (C.sub.6 H.sub.5)                 4    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            2    CH.sub.2 (2-FC.sub.6 H.sub.4)              4    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   4    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-ClC.sub.6 H.sub.4)             4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        4    CH.sub.2 (2-BrC.sub.6 H.sub.4)                                                                           2    CH.sub.2 (2-BrC.sub.6 H.sub.4)             4    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  2    CH.sub.2 (2,6-Br.sub.2 C.sub.6                                                 H.sub.3)                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   4    CH.sub.2 (2-pyridyl)      2    CH.sub.2 (2-pyridyl)                       4    CH.sub.2 (2-thienyl)      2    CH.sub.2 (2-thienyl)                       4    CH.sub.2 (2-furanyl)      2    CH.sub.2 (2-furanyl)                       4    CH.sub.2 (2-tetrahydrofuranyl)                                                                           2    CH.sub.2 (2-tetrahydrofuranyl)             4    CH.sub.2 (2-tetrahydropyranyl)                                                                           2    CH.sub.2 (2-tetrahydropyranyl)             4    Q-1                       2    Q-1                                        4    Q-3                       2    Q-3                                        4    Q-4                       2    Q-4                                        4    Q-6                       2    Q-6                                        4    Q-7                       2    Q-7                                        4    Q-8                       2    Q-8                                        4    Q-15                      2    Q-15                                       4    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  2    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   2    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         2    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           4    CH.sub.2 (2-(CF.sub.3)C.sub.6 H.sub.4)                                                                   2    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                    3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        3    CH.sub.2 (2-Br.sub.2 C.sub.6 H.sub.4)                                                                    4    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2,6-Br.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-BrC.sub.6 H.sub.3)           3    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-pyridyl)      4    CH.sub.2 (2-pyridyl)                       3    CH.sub.2 (2-thienyl)      4    CH.sub.2 (2-thienyl)                       3    CH.sub.2 (2-furanyl)      4    CH.sub.2 (2-furanyl)                       3    CH.sub.2 (2-tetrahydrofuranyl)                                                                           4    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             3    Q-1                       4    Q-1                                        3    Q-3                       4    Q-3                                        3    Q-4                       4    Q-4                                        3    Q-6                       4    Q-6                                        3    Q-7                       4    Q-7                                        3    Q-8                       4    Q-8                                        3    Q-15                      4    Q-15                                       3    CH.sub.2 (2-(OCH.sub.3)C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(OCH.sub.3)C.sub.6                                                 H.sub.4)                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)                                                                         4    CH.sub.2 (2-(CN)C.sub.6 H.sub.4)           3    CH.sub.2 (2-(CF.sub.3 )C.sub.6 H.sub.4)                                                                  4    CH.sub.2 (2-(CF.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4                                                                  4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4                                         R.sup.3 = R.sup.4 = R.sup.1 = CH.sub.3,                                                                       R.sup.3 = R.sup.4 = R.sup.1 =                                                  CH.sub.3,                                       R.sup.5 = R.sup.6 = H          R.sup.5 = R.sup.6 = H                      2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub. 3)                                                                     4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC6H.sub.4)  4    CH.sub.2 (2-BrC6H.sub.4)                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl                                                                            4    CH.sub.2 (2-tetrahydrofuranyl              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-(CHCH.sub.2 )C.sub.6                                               H.sub.4)                                        R.sup.1 = R.sup.5 = CH.sub.3,  R.sup.1 = R.sup.5 = CH.sub.3,                   R.sup.3 = R.sup.4 = H, R.sup.6 = H                                                                            R.sup.3 = R.sup.4 = H, R.sup.6 =                                               OCH.sub.3                                  2    CH.sub.2 (CH.sub.6 H.sub.5)                                                                              4    CH.sub.2 (CH.sub.6 H.sub.5)                2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC6H.sub.4)  4    CH.sub.2 (2-BrC6H.sub.4)                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub. 4)                                                                  4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl                                                                            4    CH.sub.2 (2-tetrahydrofuranyl              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC.sub.6 H.sub.4)             3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3                                                                   3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                        R.sup.1 = CH.sub.3,            R.sup.1 = CH.sub.3,                             R.sup.3 =  R.sup.4 = R.sup.5 = H,                                                                             R.sup.3 = R.sup.4 = R.sup.5 = H,                R.sup.6 = OCH.sub.3            R.sup.6 = OCH.sub.3                        2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC6H.sub.4)  4    CH.sub.2 (2-BrC6H.sub.4)                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl                                                                            4    CH.sub.2 (2-tetrahydrofuranyl              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   2    Q-1                       n    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (BrC.sub.6 H.sub.4)               3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl)             3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropropanol)            3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                        R.sup.4 = R.sup.1 = CH.sub.3,  R.sup.4 = R.sup.1 = CH.sub.3,                   R.sup.3 = R.sup.5 = R.sup.6 = H                                                                               R.sup.3 =  R.sup.5 = R.sup.6 = H           2    CH.sub.2 (C.sub.6 H.sub.5)                                                                               4    CH.sub.2 (C.sub.6 H.sub.5)                 2    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            4    CH.sub.2 (2-FC.sub.6 H.sub.4)              2    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,6-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           4    CH.sub.2 (2-ClC.sub.6 H.sub.4)             2    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  4    CH.sub.2 (2,6-Cl.sub.2 C.sub.6                                                 H.sub.3)                                   2    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      4    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)        2    CH.sub.2 (2-BrC6H.sub.4)  4    CH.sub.2 (2-BrC6H.sub.4)                   2    CH.sub.2 (2-(CH.sub.3)C.sub.6 H.sub.4)                                                                   4    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   2    CH.sub.2 (2-tetrahydrofuranyl                                                                            4    CH.sub.2 (2-tetrahydrofuranyl              2    CH.sub.2 (2-tetrahydropyranyl)                                                                           4    CH.sub.2 (2-tetrahydropyranyl)             2    CH.sub.2 (2,4-F.sub.2 C.sub.6 H.sub.3)                                                                   4    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   2    CH.sub.2 (2-(CHCH.sub.2)C.sub.6 H.sub.4)                                                                 4    CH.sub.2 (2-(CH CH.sub.2)C.sub.6                                               H.sub.4)                                   2    Q-1                       4    Q-1                                        3    CH.sub.2 (C.sub.6 H.sub.5)                                                                               3    CH.sub.2 (2-BrC6H.sub.4)                   3    CH.sub.2 (2-FC.sub.6 H.sub.4)                                                                            3    CH.sub.2 (2-(CH.sub.3)C.sub.6                                                  H.sub.4)                                   3    CH.sub.2 (2,6-F.sub.2 C.sub.6 H.sub.3)                                                                   3    CH.sub.2 (2-tetrahydrofuranyl              3    CH.sub.2 (2-ClC.sub.6 H.sub.4)                                                                           3    CH.sub.2 (2-tetrahydropyranyl)             3    CH.sub.2 (2,6-Cl.sub.2 C.sub.6 H.sub.3)                                                                  3    CH.sub.2 (2,4-F.sub.2 C.sub.6                                                  H.sub.3)                                   3    CH.sub.2 (2-Cl, 6-FC.sub.6 H.sub.3)                                                                      3    CH.sub.2 (2-(CHCH.sub.2)C.sub.6                                                H.sub.4)                                   __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

    ______________________________________                                                     Weight Percent*                                                                Active                                                                         Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredients plus at least one of a surfactant or a diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y., 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carries or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-59ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. G. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE A

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      60%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       sodium alkylnaphthalenesulfonate                                                                          2%                                                  sodium liginsulfonate      2%                                                  synthetic amorphous silica                                                                               36%                                                  ______________________________________                                    

The active ingredient is first sprayed onto the amorphous silica, then the ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE B Wettable Powder

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      50%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       sodium alkylnaphthalenesulfonate                                                                          2%                                                  low viscosity methyl cellulose                                                                            2%                                                  diatomaceous earth        46%                                                  ______________________________________                                    

The active ingredient is first sprayed onto the diatomaceous earth, then the ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE C Granule

    ______________________________________                                         Wettable Powder of Example B                                                                          5%                                                      attapulgite granules  95%                                                      ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE D Emulsifiable Concentrate

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      40%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       Atlox 3404F                3%                                                  Atlox 3404F                3%                                                  xylene                    54%                                                  ______________________________________                                    

The active ingredient and Atlox emulsifiers are dissolved in the solvent, filtered and packaged. Atlox 3403F and 3404F are blends of anionic and ionic emulsifiers from ICI Americas, Inc.

EXAMPLE E Low Strength Granule

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                       5%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       attapulgite granules      95%                                                  (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE F Low Strength Granule

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      50%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       wetting agent              1%                                                  crude ligninsulfonate salt                                                                               10%                                                  (containing 5-20% of the natural sugars)                                       attapulgite clay          39%                                                  ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1% . The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE G Concentrated Emulsion

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      25%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       xylene                    25%                                                  Atlox 3404F                5%                                                  G1284                      5%                                                  ethylene glycol            8%                                                  water                     32%                                                  ______________________________________                                    

The active ingredient, solvent and emulsifiers are blended together. This solution is added to a mixture of the ethylene glycol and water with stirring.

EXAMPLE H Solution

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                       5%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       water                     95%                                                  ______________________________________                                    

The compound is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE I Dust

    ______________________________________                                         (1α,2α,4α,5β,6α)-(+/-)-5-[(2-chloro-6-                                      10%                                                  fluorophenyl)methoxy]-6-methyl-7-oxatricyclo-                                  [4.2.1.0.sup.2,4 ]nonane                                                       attapulgite               10%                                                  Pyrophyllite              80%                                                  ______________________________________                                    

The active ingredient is sprayed onto the attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

UTILITY

Test results indicate compounds of this invention are active postemergence and, in particular, preemergence herbicides. Many compounds in this invention are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops such as barley (Hordeum vulgare), corn (Zea mays), cotton (Gossypium hirsutum), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), wheat (Triticum aestiyum), and to vegetable crops. Grass and broadleaf weed species controlled include, but are not limited to, barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), crabgrass (Digitaria spp.), duck salad (Heteranthera limosa), foxtail (Setaria spp.), velvetleaf (Afutilon theophrasti), lambsquarters (Chenopodium spp.), and umbrella sedge (Cyperus difformis). Several compounds in this invention are particularly useful for the control of barnyardgrass and selected broadleaf weeds such as duck salad and umbrella sedge in upland and paddy rice. Compound 3 in Table C demonstrates outstanding control of barnyardgrass, duck salad and umbrella sedge with no injury to rice.

Effective rates of application for compounds of this invention are determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, the effective rates of application for compounds of this invention are rates from 0.01 to 20 kg/ha with a preferred rate range of 0.03 to 1 kg/ha. One skilled in the art can easily determine effective application rates necessary for desired level of weed control.

Compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides, or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control.

    __________________________________________________________________________     Common Name                    Chemical Name                                   __________________________________________________________________________     acetochlor                     2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-                                        methylphenyl)acetamide                          acifluorfen                    5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                       2-nitrobenzoic acid                             aclonifen                      2-chloro-6-nitro-3-phenoxybenzenamine           acrolein                       2-propenal                                      alachlor                       2-chloro-N-(2,6-diethylphenyl)-N-                                              (methoxymethyl)acetamide                        alloxydim                      methyl 2,2-dimethyl-4,6-dioxo-5-[1-[(2-                                        propenyloxy)amino]butylidene] cyclo-                                           hexanecarboxylate                               ametryn                        N-ethyl-N'-(1-methylethyl)-6-(methyl-                                          thio)-1,3,5-triazine-2,4-diamine                amitrole                       1H-1,2,4-triazol-3-amine                        AMS                            ammonium sulfamate                              anilofos                       S-[2-[(4-chlorophenyl)(1-methylethyl)                                          amino]-2-oxoethyl] O,O-dimethyl                                                phosphorodithioate                              asulam                         methyl [(4-aminophenyl)sulfonyl]-                                              carbamate                                       atrazine                       6-chloro-N-ethyl-N'-(1-methylethyl)-                                           1,3,5-triazine-2,4-diamine                      aziprotryne                    4-azido-N-(1-methylethyl)-6-methylthio-                                        1,3,5-triazin-2-amine                           azoluron                       N-(1-ethyl-1H-pyrazol-5-yl)-N'-phenyl-                                         urea                                            barban                         4-chloro-2-butynyl 3-chlorocarbamate            benazolin                      4-chloro-2-oxo-3(2H)-benzothiazole-                                            acetic acid                                     benfluralin                    N-butyl-N-ethyl-2,6-dinitro-4-(tri-                                            fluoromethyl)benzenamine                        bensulfuron                    2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)-                                          amino]methylcarbonyl]aino]sulfonyl]-                                           methyl]benzoic acid, methyl ester               bensulide                      O,O-bis(1-methylethyl) S-[2-[(phenyl-                                          sulfonyl)amino]ethyl]phosphorodi-                                              thioate                                         bentazon                       3-(1-methylethyl)-(1H)-2,1,3-benzo-                                            thiadiazin-4(3H)-one, 2,2-dioxide               benzofluor                     N-[4-(ethylthio)-2-(trifluoromethyl)-                                          phenyl]methanesulfonamide                       benzoylprop                    N-benzoyl-N-(3,4-dichlorophenyl)-DL-                                           alanine                                         benzthiazuron                  N-2-benzothiazolyl-N'-methylurea                bialaphos                      4-(hydroxymethylphosphinyl)-L-2-amino-                                         butanoyl-L-alanyl-L-alanine                     bifenox                        methyl 5-(2,4-dichlorophenoxy)-2-nitro-                                        benzoate                                        bromacil                       5-bromo-6-methyl-3-(1-methylpropyl)-2,4-                                       (1H,3H)pyrimidinedione                          bromobutide                    (+)2-bromo-3,3-dimethyl-N-(1-methyl-1-                                         phenylethyl)butanamide                          bromofenoxim                   3,5-dibromo-4-hydroxybenzaldhyde O-(2,4-                                       dinitrophenyl)oxime                             bromoxynil                     3,5-dibromo-4-hydroxybenzonitrile               bromuron                       N'-(4-bromophenyl)-N,N-dimethylurea             buminafos                      dibutyl [1-(butylamino)cyclohexyl]-                                            phosphonate                                     butachlor                      N-(butoxymethyl)-2-chloro-N-(2,6-                                              diethylphenyl)acetamide                         butamifos                      O-ethyl O-(5-methyl-2-nitrophenyl)-                                            (1methylpropyl)phosphoramidothioate             buthidazole                    3-[5-(1,1-dimethylethyl)-1,3,4-thia-                                           diazol-2-yl]-4-hydroxy-1-methyl-2-                                             imidazolidinone                                 butralin                       4-(1,1-dimethylethyl)-N-(1-methyl-                                             propyl)-2,6-dinitrobenzenamine                  butylate                       S-ethyl bis(2-methylpropyl)carbamo-                                            thioate                                         cacodylic acid                 dimethyl arsinic oxide                          carbetamide                    (R)-N-ethyl-2-[[(phenylamino)carbonyl]-                                        oxy]propanamide                                 CDAA                           2-chloro-N,N-di-2-propenylacetamide             CDEC                           2-chloroallyl diethyldithiocarbamate            chlomethoxyfen                 4-(2,4-dichlorophenoxy)-2-methoxy-1-                                           nitrobenzene                                    chloramben                     3-amino-2,5-dichlorobenzoic acid                chlorbromuron                  3-(4-bromo-3-chlorophenyl)-1-methoxy-1-                                        methylurea                                      chlorbufam                     1-methyl-2-propynl(3-chlorophenyl)-                                            carbamate                                       chlorfenac                     2,3,6-trichlorobenzeneacetic acid               chlorflurecol-                 methyl 2-chloro-9-hydroxy-9H-fluorene-          methyl                         methyl 9-carboxylate                            chloridazon                    5-amino-4-chloro-2-phenyl-3(2H)-                                               pyridazinone                                    chlorimuron                    2-[[[[(4-chloro-6-methoxy-2-                                                   pyrimidinyl)ethylamino]carbonyl]amino]                                         sulfonyl]benzoic acid, ethyl ester              chlornitrofen                  1,3,5-trichloro-2-(4-nitrophenoxy)-                                            benzene                                         chloropicrin                   trichloronitromethane                           chloroxuron                    N'-[4-(4-chlorophenoxy)phenyl]-N,N-                                            dimethylurea                                    chlorpropham                   1-methylethyl 3-chlorophenylcarbamate           chlorsulfuron                  2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-                                        triazin-2-yl)amino]carbonyl]-                                                  benzenesulfonamide                              chlorthal-                     dimethyl 2,3,5,6-tetrachloro-1,4-               dimethyl                       benzenedicarboxylate                            chlorthiamid                   2,6-dichlorobenzene carbothioamide              chlortoluron                   N'-(3-chloro-4-methylphenyl)-N,N-                                              dimethylurea                                    cinmethylin                    exo-1-methyl-4-(1-methylethyl)-2-[(2-                                          methylphenyl)methoxy]-7-oxabicyclo-                                            [2.2.1]heptane                                  clethodim                      (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)-                                     oxy]imino]propyl]-5-[2-(ethylthio)-                                            propyl]-3-hydroxy-2-cyclohexen-1-one            clomazone                      2-[(2-chlorophenyl)methyl]-4,4-dimethyl-                                       3-isoxazolidinone                               cloproxydim                    (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)-                                        imino]butyl]-5-[2-(ethylthio)propyl]-                                          3-hydroxy-2-cyclohexen-1-one                    clopyralid                     3,6-dichloro-2-pyridinecarboxylic acid          CMA                            calcium salt of MAA                             cyanazine                      2-[[4-chloro-6-(ethylamino)-1,3,5-                                             triazin-2-yl]amino]-2-methylpropane-                                           nitrile                                         cycloate                       S-ethyl cyclohexylethylcarbamothioate           cycloxydim                     2-[1-ethoxyimino)butyl]-3-hydroxy-5-                                           (tetrahydro-2H-thiopyran-3-yl)-2-                                              cyclohexene-1-one                               cycluron                       3-cyclooctyl-1,1-dimethylurea                   cyperquat                      1-methyl-4-phenylpyridinium                     cyprazine                      2-chloro-4-(cyclopropylamino)-6-(iso-                                          propylamino)- .sub.- s-triazine                 cyprazole                      N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-                                       thiadiazol-2-                                                                  yl]cyclopropanecarboxamide                      cypromid                       3',4'-dichlorocyclopropanecarboxanilide         dalapon                        2,2-dichloropropanoic acid                      dazomet                        tetrahydro-3,5-dimethyl-2H-1,3,5-thia-                                         diazine-2-thione                                DCPA                           dimethyl 2,3,5,6-tetrachloro-1,4-                                              benzenedicarboxylate                            desmedipham                    ethyl [3-[[(phenylamino)carbonyl]oxy]-                                         phenyl]carbamate                                desmetryn                      2-(isopropylamino)-4-(methylamino)-6-                                          (methylthio)- .sub.- s-triazine                 diallate                       S-(2,3-dichloro-2-propenyl)bis(1-                                              methylethyl)carbamothioate                      dicamba                        3,6-dichloro-2-methoxybenzoic acid              dichlobenil                    2,6-dichlorobenzonitrile                        dichlorprop                    (±)-2-(2,4-dichlorophenoxy)propanoic                                        acid                                            diclofop-                      (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]                                      -                                               methyl                         propanoic acid, methyl ester                    diethatyl                      N-(chloroacetyl)-N-(2,6-diethylphenyl)-                                        glycine                                         difenoxuron                    N'-[4-(4-methoxyphenoxy)phenyl]-N,N-                                           dimethylurea                                    difenzoquat                    1,2-dimethyl-3,5-diphenyl-1H-pyrazolium                                        ion                                             diflufenican                   N-(2,4-difluorophenyl)-2-(3-trifluoro-                                         methylphenoxy)pyridine-3-carboxamide            dimefuron                      N'-[3-chloro-4-[5-(1,1-dimethylethyl)-2-                                       oxo-1,3,4-oxadiazol-3(2H)-yl]phenyl]-                                          N,N-dimethylurea                                dimethachlor                   2-chloro-N-(2,6-dimethylphenyl)-N-(2-                                          methoxyethyl)acetamide                          dimethametryn                  N-(1,2-dimethylpropyl)-N'-ethyl-6-                                             (methylthio)-1,3,5-triazine-2,4-                                               diamine                                         dimethipin                     2,3-dihydro-5,6-dimethyl-1,4-dithiin                                           1,1,4,4-tetraoxide                              dimethylarsinic                dimethylarsinic acid                            dinitramine                    N.sup.3,N.sup.3-diethyl-2,4-dinitro-6-(trif                                    luoro-                                                                         methyl)-1,3-benzenediamine                      dinoseb                        2-(1-methylpropyl)-4,6-dinitrophenol            dinoterb                       2-(1,1-dimethylethyl)-4,6-dinitrophenol         diphenamid                     N,N-dimethyl-α-phenylbenzeneacetamide     dipropetryn                    6-(ethylthio)-N,N'-bis(1-methylethyl)-                                         1,3,5-triazine-2,4-diamine                      diquat                         6,7-dihydrodipyrido[1,2-a:2',1'-c]-                                            pyrazinediium ion                               diuron                         N'-(3,4-dichlorophenyl)-N,N-dimethylurea        DNOC                           2-methyl-4,6-dinitrophenol                      DPX-V9360                      2-[[(4,6-dimethoxypyrimidin-2-yl)amino-                                        carbonyl]aminosulfonyl]-N,N-dimethyl                                           3-pyridinecarboxamide                           DSMA                           disodium salt of MAA                            dymron                         N-(4-methylphenyl)-N'-(1-methyl-1-                                             phenylethyl)urea                                eglinazine-                    N-[4-chloro-6-(ethylamino)-1,3,5-               ethyl                          triazin-2-yl]glycine ethyl ester                endothall                      7-oxabicyclo[2.2.1]heptane-2,3-                                                dicarboxylic acid                               EPTC                           S-ethyl dipropylcarbamothioate                  ethalfluralin                  N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                           dinitro-4-(trifluoromethyl)benzen-                                             amine                                           ethidimuron                    N-[5-(ethylsulfonyl)-1,3,4-thiadiazol-2-                                       yl]-N,N'-dimethylurea                           ethofumesate                   (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-5-                                    benzofuranyl methanesulfonate                   fenac                          2,3,6-trichlorobenzeneacetic acid               fenoprop                       (±)-2-(2,4,5-trichlorophenoxy)propanoic                                     acid                                            fenoxaprop                     (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]-                                    phenoxy]propanoic acid                          fenuron                        N,N-dimethyl-N'-phenylurea                      fenuron TCA                    Salt of fenuron and TCA                         flamprop-M-                    1-methylethyl N-benzoyl-N-(3-chloro-4-          isopropyl                      fluorophenyl)-D-alanine                         flamprop-methyl                methyl N-benzoyl-N-(3-chloro-4-                                                fluorophenyl)-DL-alaninate                      fluazifop                      (±)-2-[4-[[5-(trifloromethyl)-2-                                            pyridinyl]oxy]phenoxy]propanoic acid            fluazifop-P                    (R)-2-[4-[[5-(trifluoromethyl)-2-                                              pyridinyl]oxy]phenoxy]propanoic acid            fluchloralin                   N-(2-chloroethyl)-2,6-dinitro-N-propyl-                                        4-(trifluoromethyl)benzenamine                  fluometuron                    N,N-dimethyl-N'-[3-(trifluoromethyl)-                                          phenyl]urea                                     fluralin                       N-butyl-N-ethyl-2,6-dinitro-4-                                                 (trifluoromethyl)benzenamine                    fluorodifen                     -p-nitrophenyl α,α,α-tri                                    fluoro-2-nitro- -p-                                                            tolyl ether                                     fluorogly-                     carboxymethyl 5-[2-chloro-4-(trifluoro-         cofen                          methyl)phenoxy]-2-nitrobenzoate                 flurecol-butyl                 butyl 9-hydroxy-9H-fluorene-9-                                                 carboxylate                                     fluridone                      1-methyl-3-phenyl-5-[3-(trifluoro-                                             methyl)phenyl]-4(1H)-pyridinone                 flurochloridone                3-chloro-4-(chloromethyl)-1-[3-                                                (trifluoromethyl)phenyl]-2-                                                    pyrrolidinone                                   fluroxypyr                     [(4-amino-3,5-dichloro-6-fluoro-2-                                             pyridinyl)oxy]acetic acid                       fomesafen                      5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                       N-(methylsulfonyl)-2-nitrobenzamide             fosamine-                      ethyl hydrogen (aminocarbonyl)-                 ammonium                       phosphonate ammonium ethyl                      glufosinate-                   ammonium 2-amino-4-(hydroxymethylphos-          ammonium                       phinyl)butanoate                                glyphosate                     N-(phosphonomethyl)glycine                      haloxyfop                      2-[4-[[3-chloro-5-(trifluoromethyl)-2-                                         pyridinyl]oxy]phenoxy]propanoic acid            hexaflurate                    potassium hexafluoroarsenate                    hexazinone                     3-cyclohexyl-6-(dimethylamino)-1-methyl-                                       1,3,5-triazine-2,4 (1H,3H)-dione                imazamethabenz                 6-(4-isopropyl-4-methyl-5-oxo-2-                                               imidazolin-2-yl)- .sub.-- m-toluic acid,                                       methyl                                                                         ester and 6-(4-isopropyl-4-methyl-5-                                           oxo-2-imidazolin-2-yl)-p-toluic acid,                                          methyl ester                                    imazapyr                       (±)-2-[4,5-dihydro-4-methyl-4-(1-                                           methylethyl)-5-oxo-1H-imidazol-2-yl]-                                          3-pyridinecarboxylic acid                       imazaquin                      2-[4,5-dihydro-4-methyl-4-(1-methyl-                                           ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                              quinolinecarboxylic acid                        imazethapyr                    (±)-2-[4,5-dihydro-4-methyl-4-(1-                                           methylethyl)-5-oxo-1H-imidazol-2-yl]-                                          5-ethyl-3-pyridinecarboxylic acid               ioxynil                        4-hydroxy-3,5-diiodobenzonitrile                isocarbamid                    N-(2-methylpropyl)-2-oxo-1-                                                    imidazolidine-carboxamide                       isopropalin                    4-(1-methylethyl)-2,6-dinitro-N,N-                                             dipropylbenzenamine                             isoproturon                    N-(4-isopropylphenyl)-N',N'-dimethylurea        isouron                        N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]-                                       N,N-dimethylurea                                isoxaben                       N-[3-(1-ethyl-1-methylpropyl)-5-                                               isoxazolyl]-2,6-dimethoxybenzamide              karbutilate                    3-[[(dimethylamino)carbonyl]amino]-                                            phenyl-(1,1-dimethylethyl)carbamate             lactofen                       (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-                                      chloro-4-(trifluoromethyl)phenoxy]-2-                                          nitrobenzoate                                   lenacil                        3-cyclohexyl-6,7-dihydro-1H-cyclopenta-                                        pyrimidine-2,4(3H,5H)-dione                     linuron                        N'-(3,4-dichlorophenyl)-N-methoxy-N-                                           methylurea                                      MAA                            methylarsonic acid                              MAMA                           monoammonium salt of MAA                        MCPA                           (4-chloro-2-methylphenoxy)acetic acid           MCPA-thioethyl                 S-ethyl (4-chloro-2-methylphenoxy)-                                            ethanethioate                                   MCPB                           4-(4-chloro-2-methylphenoxy)butanoic                                           acid                                            mecoprop                       (±)-2-(4-chloro-2-methylphenoxy)-                                           propanoic acid                                  mefenacet                      2-(2-benzothiazolyloxy)-N-methyl-N-                                            phenyl acetamide                                mefluidide                     N-[2,4-dimethyl-5-[[(trifluoromethyl)-                                         sulfonyl]amino]phenyl]acetamide                 metamitron                     4-amino-3-methyl-6-phenyl-1,2,4-triazin-                                       5(4H)-one                                       metazachlor                    2-chloro-N-(2,6-dimethylphenyl)-N-(1(H)-                                       pyrazol-1-ylmethyl)acetamide                    methabenz-                     1,3-dimethyl-3-(2-benzothiazolyl)urea           thiazuron                                                                      methal-                        N-(2-methyl-2-propenyl)-2,6-dinitro-N-          propalin                       propyl-4-(trifluoromethyl)benzenamide           metham                         methylcarbamodithioic acid                      methazole                      2-(3,4-dichlorophenyl)-4-methyl-1,2,4-                                         oxadiazolidine-3,5-dione                        methoxuron                     N'-(3-chloro-4-methoxyphenyl)-N,N-                                             dimethylurea                                    methoxyphenone                 (4-methoxy-3-methylphenyl)(3-methyl-                                           phenyl)methanone                                methyldymron                   N-methyl-N'-(1-methyl-1-phenylethyl)-N-                                        phenylurea                                      metobromuron                   N'-(4-bromophenyl)-N-methoxy-N-                                                methylurea                                      metolachlor                    2-chloro-N-(2-ethyl-6-methylphenyl)-N-                                         (2-methoxy-1-methylethyl)acetamide              metoxuron                      N'-(3-chloro-4-methoxyphenyl)-N,N-                                             dimethylurea                                    metribuzin                     4-amino-6-(1,1-dimethylethyl)-3-                                               (methylthio)-1,2,4-triazin-5(4H)-one            metsulfuron                    2-[[[[(4-methoxy-6-methyl-1,3,5-tri-            methyl                         azin-2-yl)amino]carbonyl]amino]-                                               sulfonyl]benzoic acid, methyl ester             MH                             1,2-dihydro-3,6-pyridazinedione                 molinate                       S-ethyl hexahydro-1H-azepine-1-carbo-                                          thioate                                         monalide                       N-(4-chlorophenyl)-2,2-dimethyl-                                               pentanamide                                     monolinuron                    3-( -p-chlorophenyl)-1-methoxy-1-                                              methylurea                                      monuron                        N'-(4-chlorophenyl)-N,N-dimethylurea            MSM                            monosodium salt of MAA                          naproanilide                   2-(2-naphthalenyloxy)-N-phenyl-                                                propanamide                                     napropamide                    N,N-diethyl-2-(1-naphthalenyloxy)-                                             propanamide                                     naptalam                       2-[(1-naphthalenylamino)carbonyl]-                                             benzoic acid                                    neburon                        1-butyl-3-(3,4-dichlorophenyl)-1-                                              methylurea                                      nitralin                       4-methylsulfonyl-2,6-dinitro-N,N-                                              dipropylaniline                                 nitrofen                       2,4-dichloro-1-(4-nitrophenoxy)benzene          nitrofluorfen                  2-chloro-1-(4-nitrophenoxy)-4-                                                 (trifluoromethyl)benzene                        norea                          N,N-dimethyl-N'-(octahydro-4,7-methano-                                        1H-inden-5-yl)urea 3aα,4α,5.alp                                    ha.,7α,7aα-                                                        isomer                                          norflurazon                    4-chloro-5-(methylamino)-2-[3-(tri-                                            fluoromethyl)phenyl]-3(2H)-                                                    pyridazinone                                    orbencarb                      S-[2-(chlorophenyl)methyl]diethyl-                                             carbamothioate                                  oryzalin                       4-(dipropylamino)-3,5-dinitro-                                                 benzenesulfonamide                              oxadiazon                      3-[2,4-dichloro-5-(1-methylethoxy)-                                            phenyl]-5-(1,1-dimethylethyl)-1,3,4-                                           oxadiazol-2(3H)-one                             oxyfluorfen                    2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-                                        (trifluoromethyl)benzene                        paraquat                       1,1'-dimethyl-4,4'-dipyridinium ion             pebulate                       S-propyl butylethylcarbamothioate               pendimethalin                  N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                            dinitrobenzenamine                              perfluidone                    1,1,1-trifluoro-N-[2-methyl-4-                                                 (phenylsulfonyl)phenyl]methane-                                                sulfonamide                                     phenisopham                    3-[[(1-methylethoxy)carbonyl]amino]-                                           phenyl ethylphenylcarbamate                     phenmedipham                   3-[(methoxycarbonyl)amino]phenyl (3-                                           methylphenyl)carbamate                          picloram                       4-amino-3,5,6-trichloro-2-pyridine-                                            carboxylic acid                                 piperophos                     S-[2-(2-methyl-1-piperidinyl)-2-oxo-                                           ethyl]O,O-dipropyl phosphorodithioate           pretilachlor                   2-chloro-N-(2,6-diethylphenyl)-N-(2-                                           propoxyethyl)acetamide                          procyazine                     2-[[4-chloro-6-(cyclopropylamino)-1,3,5-                                       triazine-2-yl]amino]-2-methylpropane-                                          nitrile                                         prodiamine                     2,4-dinitro-N3,N3-dipropyl-6-(trifluoro-                                       methyl)-1,3-benzenediamine                      profluralin                    N-(cyclopropylmethyl)-2,6-dinitro-N-                                           propyl-4-(trifluoromethyl)benzenamine           proglinazine-                  N-[4-chloro-6-[(1-methylethyl)amino]-           ethyl                          1,3,5-triazin-2-yl]glycine ethyl ester          prometon                       6-methoxy-N,N'-bis(1-methylethyl)-1,3,5-                                       triazine-2,4-diamine                            prometryn                      N,N'-bis(1-methylethyl)-6-(methylthio)-                                        1,3,5-triazine-2,4-diamine                      pronamide                      3,5-dichloro-N-(1,1-dimethyl-2-                                                propynyl)benzamide                              propachlor                     2-chloro-N-(1-methylethyl)-N-phenyl-                                           acetamide                                       propanil                       N-(3,4-dichlorophenyl)propanamide               propaquizafop                  2-[[(1-methylethylidene)amino]oxy]ethyl                                        2-[4-[(6-chloro-2-quinoxalinyl)oxy]-                                           phenoxy]propanoate                              propazine                      6-chloro-N,N'-bis(1-methylethyl)-1,3,5-                                        triazine-2,4-diamine                            propham                        1-methylethyl phenylcarbamate                   propyzamide                    3,5-dichloro-N-(1,1-dimethyl-2-propynl)-                                       benzamide                                       prosulfalin                    N-[[4-(dipropylamino)-3,5-dinitro-                                             phenyl]sulfonyl]-S,S-dimethyl-                                                 sulfilimine                                     prosulfocarb                   S-benzyldipropylthiocarbamate                   prynachlor                     2-chloro-N-(1-methyl-2-propynyl)-                                              acetanilide                                     pyrazon                        5-amino-4-chloro-2-phenyl-3(2H)-                                               pyridazinone                                    pyrazosulfuron-                ethyl 5-[[[[(4,6-dimethoxy-2-                   ethyl                          pyrimidinyl)amino]carbonyl]amino]-                                             sulfonyl]-1-methyl-1H-pyrazole-4-                                              carboxylate                                     pyrazoxyfen                    2-[[4-(2,4-dichlorobenzoyl)-1,3-                                               dimethyl-1H-pyrazol-5-yl]oxy]-1-                                               phenylethanone                                  pyridate                       O-(6-chloro-3-phenyl-4-pyridazinyl) S-                                         octyl carbonothioate                            quizalofop                     (±)-2-[4-[(6-chloro-2-quinoxalinyl)-         ethyl                          oxy]phenoxy]propanoic acid, ethyl                                              ester                                           secbumeton                     N-ethyl-6-methoxy-N'-(1-methylpropyl)-                                         1,3,5-triazine-2,4-diamine                      sethoxydim                     2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                          thio)propyl]-3-hydroxy-2-cyclohexen-1-                                         one                                             siduron                        N-(2-methylcyclohexyl)-N'-phenylurea            simazine                       6-chloro-N,N'-diethyl-1,3,5-triazine-                                          2,4-diamine                                     simetryn                       N,N'-diethyl-6-(methylthio)-1,3,5-                                             triazine-2,4-diamine                            sodium chlorate                sodium chlorate                                 sodium mono-                   chloroacetic acid, sodium salt                  chloroacetate                                                                  sulfometuron                   2-[[[[(4,6-dimethyl-2-pyrimidinyl)-             methyl                         amino]carbonyl]amino]sulfonyl]-benzoic                                         acid, methyl ester                              2,4,5-T                        (2,4,5-trichlorophenoxy)acetic acid             2,3,6-TBA                      2,3,6-trichlorobenzoic acid                     TCA                            trichloroacetic acid                            tebutam                        2,2-dimethyl-N-(1-methylethyl)-N-                                              (phenylmethyl)propanamide                       tebuthiuron                    N-[5-(1,1-dimethylethyl)-1,3,4-                                                thiadiazol-2-yl]-N,N'-dimethylurea              terbacil                       5-chloro-3-(1,1-dimethylethyl)-6-methyl-                                       2,4(1H,3H)-pyrimidinedione                      terbuchlor                     N-(butoxymethyl)-2-chloro-N-[2-(1,1-                                           dimethylethyl)-6-methylphenyl]-                                                acetamide                                       terbumeton                     N-(1,1-dimethylethyl)-N'  -ethyl-6-                                            methoxy-1,3,5-triazine-2,4-diamine              terbuthylazine                 2-(tert-butylamino)-4-chloro-6-(ethyl-                                         amino)- .sub.- s-triazine                       terbutol                       2,6-di-tert-butyl- -p-tolyl methyl-                                            carbamate                                       terbutryn                      N-(1,1-dimethylethyl)-N'-ethyl-6-                                              (methylthio)-1,3,5-triazine-2,4-                                               diamine                                         thifensulfuron                 3-[[[[(4-methoxy-6-methyl-1,3,5,triazin-                                       2-yl)amino]carbonyl]amino]sulfonyl]-2-                                         thiophenecarboxylic acid, methyl ester          thiameturon-                   methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-         methyl                         triazin-2-yl)amino]carbonyl]amino]-                                            sulfonyl]2-thiophenecarboxylate                 thiazafluron                   N,N'-dimethyl-N-[5-(trifluoromethyl)-                                          1,3,4-thiadiazol-2-yl]urea                      thiobencarb                    S-[(4-chlorophenyl)methyl]diethylcar-                                          bamothioate                                     tiocarbazil                    S-(phenylmethyl) bis(1-methylpropyl)-                                          carbamothioate                                  tralkoxydim                    2-[1-(ethoxyimino)propyl]-3-hydroxy-5-                                         (2,4,6-trimethylphenyl)-2-cyclohexen-                                          1-one                                           triallate                      S-(2,3,3-trichloro-2-propenyl) bis(1-                                          methylethyl)carbamothioate                      triasulfuron                   2-(2-chloroethoxy)-N-[[(4-methoxy-6-                                           methyl-1,3,5-triazin-2-yl)amino]-                                              carbonyl]benzenesulfonamide                     tribenuron                     2-[[[[N-(4-methoxy-6-methyl-1,3,5-              methyl                         triazine-2-yl)-N-methylamino]-                                                 carbonyl]amino]-sulfonyl]benzoic acid,                                         methyl ester                                    triclopyr                      [(3,5,6-trichloro-2-pyridinyl)oxy]-                                            acetic acid                                     tridiphane                     (+)2-(3,5-dichlorophenyl)-2-(2,2,2-                                            trichloroethyl)oxirane                          trietazine                     6-chloro-N,N,N'-triethyl-1,3,5-triazine-                                       2,4-diamine                                     trifluralin                    2,6-dinitro-N,N-dipropyl-4-(trifluoro-                                         methyl)benzenamine                              trimeturon                     1-( -p-chlorophenyl)-2,3,3-trimethyl-                                          pseudourea                                      2,4-D                          (2,4-dichlorophenoxy)acetic acid                2,4-DB                         4-(2,4-dichlorophenoxy)butanoic acid            vernolate                      S-propyl dipropylcarbamothioate                 xylachlor                      2-chloro-N-(2,3-dimethylphenyl)-N-(1-                                          methylethyl)acetamide                           __________________________________________________________________________

Herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. Test procedures and results follow.

                                      COMPOUND TABLE                               __________________________________________________________________________      ##STR18##                                                                     Com-                           Physiochemical/Spectral Data                    pound R.sup.1   W              (δ in CDCl.sub.3)                         __________________________________________________________________________     1     CH.sub.3  2-Cl, 6-FPh    m.p. 69-71° C.                           2     CH.sub.3  2,4-F.sub.2 Ph NMR: 7.48 (m, 1H), 6.95(m, 1H),                                                6.79(m, 1H), 4.79(d, 1H), 4.62                                                 (d, 1H), 3.6(dd, 1H), 3.53                                                     (m, 2H), 2.60(m, 1H), 1.6                                                      (m, 1H), 1.50(dd, 2H), 1.31                                                    s, 3H), 1.1(m, 1H), 0.9(m, 1H),                                                0.58(m, 1H).                                    3     CH.sub.3  2-ClPh         NMR: 7.6(d, 1H), 7.31(D, 1H),                                                  7.11(m, 2H), 4.88(d, 1H), 4.70                                                 (d, 1H), 3.61(m, 2H), 3.55                                                     (d, 1H), 2.60(m, 1H), 1.6                                                      (m, 1H), 1.5(dd, 2H), 1.39                                                     (s, 3H), 1.16(m, 1H), 0.91                                                     (m, 1H), 0.59(m, 1H).                           4     CH.sub.3  2-F-Ph         NMR: 7.55(dd, 1H), 7.22                                                        (m, 1H), 7.10(dd, 1H), 7.01                                                    (dd, 1H), 4.82(d, 1H), 4.71                                                    (d, 1H), 3.55(m, 3H), 2.60                                                     (m, 1H), 1.60(m, 1H), 1.49                                                     (m, 2H), 1.32(s, 3H), 1.1                                                      (m, 1H), 0.9(m, 1H), 0.59                                                      (m, 1H).                                        5     CH.sub.3  Ph             NMR: 7.3(m, 5H), 4.82(d, 1H),                                                  4.61(d, 1H), 3.60(m, 1H), 3.52                                                 (m, 2H), 2.59(m, 1H), 1.6                                                      (m, 1H), 1.49(m, 2H), 1.34                                                     (s, 3H), 1.01(m, 1H), 0.90                                                     (m, 1H), 0.59(m, 1H).                           6     CH.sub.2 CH.sub.3                                                                        Ph             NMR: 7.2(m, 5H), 4.78(d, 1H),                                                  4.61(d, 1H), 3.55(m, 3H), 2.59                                                 (m, 1H), 1.7(m, 2H), 1.6-1.2                                                   (m, 3H), 1.00(m, 1H), 0.92                                                     (m, 1H), 0.72(t, 3H), 0.60                                                     (m, 1H).                                        7     CH.sub.2 CH.sub.3                                                                        2-FPh          NMR: 7.5(m, 1H), 7.3-6.92                                                      (m, 3H), 4.80(d, 1H), 4.67                                                     (d, 1H), 3.6(d, 1H), 3.55                                                      (m, 2H), 2.59(m, 1H), 1.8-1.5                                                  (m, 4H), 1.20(d, 1H), 1.1                                                      (m, 1H), 0.9(m, 1H), 0.72                                                      (t, 3H), 0.59(m, 1H).                           8     CH.sub. 2 CH.sub.3                                                                       2,6-F.sub.2 Ph m.p. 51-53° C.                           9     CH.sub.2 CH.sub.3                                                                        2-Cl, 6-FPh    m.p. 73-75° C.                           10    CH.sub.2 CH.sub.3                                                                        2-ClPh         NMR: 7.60(m, 1H), 7.2(m, 3H),                                                  4.85(d, 1H), 4.70(d, 1H), 3.64                                                 (d, 1H), 3.58(m, 2H), 2.60                                                     (m, 1H), 1.8-1.4(m, 4H), 1.30                                                  (d, 1H), 1.19(m, 1H), 0.94                                                     (m, 1H), 0.76(t, 3H), 0.60                                                     (m, 1H).                                        11    CH.sub.2 CH.sub.3                                                                        2-CH.sub.3 Ph  NMR: 7.35(m, 1H), 7.18(m, 3H),                                                 4.829d, 1H), 4.58(d, 1H), 3.55                                                 (m, 3H), 2.59(m, 1H), 2.40                                                     (s, 3H), 1.6(m, 4H), 1.5(d, 1H),                                               1.10(m, 1H), 0.92(m, 1H), 0.70                                                 (t, 3H), 0.60(m, 1H).                           12    CH.sub.3  2,6-F.sub.2 Ph NMR: 7.22(m, 1H), 6.85(t, 2H),                                                 4.89(d, 1H), 4.67(d, 1H), 3.5                                                  (m, 3H), 2.59(m, 1H), 1.65-1.1                                                 (m, 4H), 1.23(s, 3H), 0.89                                                     (m, 1H), 0.60(m, 1H).                           13    CH.sub.3  2-CH.sub.3 Ph  NMR: 7.4-7.1(m, 4H), 4.82                                                      (d, 1H), 4.59(d, 1H), 3.5                                                      (m, 3H), 2.59(m, 1H), 2.40                                                     (s, 3H), 1.31(s, 3H), 1.6-1.2                                                  (m, 3H), 1.01(m, 1H), 0.91                                                     (m, 1H), 0.6(m, 1H).                            __________________________________________________________________________

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aeastivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE A                                                          ______________________________________                                                    COMPOUND                                                            Rate (200 g/ha)                                                                             1        2      3      4    5                                     ______________________________________                                         POSTEMERGENCE                                                                  Barley       0        0      0      0    3                                     Barnyardgrass                                                                               9        4      9      9    9                                     Bedstraw     2        0      0      0    0                                     Blackgrass   0        0      0      6    2                                     Cheatgrass   0        0      0      2    2                                     Chickweed    2        0      0      0    0                                     Cocklebur    0        0      0      0    0                                     Corn         2        0      0      0    2                                     Cotton       0        0      0      0    0                                     Crabgrass    3        0      2      2    7                                     Giant foxtail                                                                               1        0      1      6    5                                     Lambsquarters                                                                               5        0      0      0    0                                     Morningglory 0        0      0      0    0                                     Nutsedge     0        0      5      0    0                                     Rape         0        0      0      0    0                                     Rice         0        2      1      2    7                                     Sorghum      0        0      0      0    0                                     Soybean      0        0      0      0    2                                     Sugar beet   0        0      0      0    2                                     Velvetleaf   4        3      5      7    3                                     Wheat        0        0      0      3    5                                     Wild oat     0        0      0      0    0                                     ______________________________________                                                    COMPOUND                                                            Rate (50 g/ha)                                                                              1        2      3      4    5                                     ______________________________________                                         POSTEMERGENCE                                                                  Barley       0        0      0      0    0                                     Barnyardgrass                                                                               5        2      7      8    6                                     Bedstraw     0        0      0      0    0                                     Blackgrass   0        0      0      0    0                                     Cheatgrass   0        0      0      0    0                                     Chickweed    0        0      0      0    0                                     Cocklebur    0        0      0      0    0                                     Corn         0        0      0      0    0                                     Cotton       0        0      0      0    0                                     Crabgrass    1        0      0      1    0                                     Giant foxtail                                                                               0        0      0      0    2                                     Lambsquarters                                                                               0        0      0      0    0                                     Morningglory 0        0      0      0    0                                     Nutsedge     0        0      0      0    0                                     Rape         0        0      0      0    0                                     Rice         0        0      2      1    2                                     Sorghum      0        0      0      0    0                                     Soybean      0        0      0      0    0                                     Sugar beet   0        0      0      0    0                                     Velvetleaf   3        0      3      3    3                                     Wheat        0        0      0      2    2                                     Wild oat     0        0      0      0    0                                     ______________________________________                                                    COMPOUND                                                            Rate (200 g/ha)                                                                             1        2      3      4    5                                     ______________________________________                                         PREEMERGENCE                                                                   Barley       2        0      0      0    0                                     Barnyardgrass                                                                               10       9      10     10   10                                    Bedstraw     6        0      6      3    6                                     Blackgrass   9        2      3      9    10                                    Cheatgrass   8        3      8      10   9                                     Chickweed    6        6      3      6    6                                     Cocklebur    7        0      0      0    0                                     Corn         5        7      5      7    4                                     Cotton       2        2      0      0    0                                     Crabgrass    8        7      9      9    10                                    Giant foxtail                                                                               10       9      10     9    10                                    Lambsquarters                                                                               8        10     8      7    9                                     Morningglory 0        0      0      0    0                                     Nutsedge     0        0      0      0    9                                     Rape         2        0      7      3    4                                     Rice         2        2      0      0    0                                     Sorghum      2        0      0      0    0                                     Soybean      0        0      0      1    0                                     Sugar beet   6        --     3      3    2                                     Velvetleaf   3        4      4      5    6                                     Wheat        0        0      0      3    2                                     Wild oat     6        4      6      6    4                                     ______________________________________                                                    COMPOUND                                                            Rate (50 g/ha)                                                                              1        2      3      4    5                                     ______________________________________                                         PREEMERGENCE                                                                   Barley       0        0      0      0    0                                     Barnyardgrass                                                                               10       9      10     10   10                                    Bedstraw     2        0      2      2    5                                     Blackgrass   6        2      3      6    7                                     Cheatgrass   0        0      0      3    2                                     Chickweed    0        0      4      5    5                                     Cocklebur    3        0      0      0    0                                     Corn         2        2      1      0    0                                     Cotton       2        2      0      0    0                                     Crabgrass    9        3      6      3    6                                     Giant foxtail                                                                               10       8      10     9    9                                     Lambsquarters                                                                               7        0      4      5    2                                     Morningglory 0        0      0      0    0                                     Nutsedge     0        0      0      0    0                                     Rape         0        0      0      0    0                                     Rice         0        2      2      0    0                                     Sorghum      0        0      0      0    0                                     Soybean      1        0      0      0    0                                     Sugar beet   0        0      0      2    0                                     Velvetleaf   5        3      2      3    2                                     Wheat        0        0      0      0    0                                     Wild oat     0        0      0      0    0                                     ______________________________________                                    

TEST B

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (paddy application), and to plants that were in the one- to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stillaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (abutilon theophrasti), wheat (Triticum aeasivum), wild buckwheat (Polygonum convolvulvus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), umbrella sedge (Cyperus difformis) and duck salad (Heteranthera limosa).

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty-one days after application of the test compound. Plant response ratings, summarized in Table B, were recorded on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE B                                                          ______________________________________                                                       COMPOUND                                                         Rate (250 g/ha) 1      3        4    5                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      0        2    3                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        9    10                                        Chickweed       0      0        0    --                                        Corn            2      0        6    5                                         Cotton          3      0        0    0                                         Crabgrass       3      0        2    2                                         Downy brome     0      0        0    0                                         Duck salad      5      8        9    9                                         Giant foxtail   3      5        2    3                                         Lambsquarters   0      0        --   --                                        Morningglory    0      0        0    3                                         Pigweed         0      0        0    4                                         Rape            0      0        0    0                                         Ryegrass        9      3        9    5                                         Sorghum         0      2        0    2                                         Soybean         2      0        0    4                                         Speedwell       0      0        0    --                                        Sugar beet      0      0        0    0                                         Velvetleaf      0      3        0    5                                         Wheat           0      0        7    3                                         Wild buckwheat  0      0        0    0                                         Wild oat        0      0        3    2                                         Barnyardgrass   10     10       10   10                                        Rice Japonica   7      7        10   9                                         Umbrella sedge  9      9        10   9                                         ______________________________________                                                       COMPOUND                                                         Rate (125 g/ha) 1      3        4    5                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      0        0    2                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        9    10                                        Chickweed       0      0        0    0                                         Corn            0      0        2    5                                         Cotton          0      0        0    0                                         Crabgrass       0      0        0    0                                         Downy brome     0      0        0    0                                         Duck salad      1      7        9    8                                         Giant foxtail   2      2        0    0                                         Lambsquarters   --     0        0    0                                         Morningglory    0      0        0    0                                         Pigweed         0      0        0    2                                         Rape            0      0        0    0                                         Ryegrass        3      0        7    3                                         Sorghum         0      0        0    0                                         Soybean         0      0        0    1                                         Speedwell       0      0        0    0                                         Sugar beet      0      0        --   0                                         Velvetleaf      0      2        0    3                                         Wheat           0      0        3    0                                         Wild buckwheat  0      0        0    0                                         Wild oat        0      0        0    0                                         Barnyardgrass   10     10       10   10                                        Rice Japonica   6      7        9    9                                         Umbrella sedge  9      9        9    9                                         ______________________________________                                                       COMPOUND                                                         Rate (62 g/ha)  1      3        4    5                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      0        0    0                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        3    2                                         Chickweed       0      0        0    0                                         Corn            0      0        0    3                                         Cotton          0      0        0    0                                         Crabgrass       0      0        0    0                                         Downy brome     0      0        0    0                                         Duck salad      0      0        7    8                                         Giant foxtail   0      0        0    0                                         Lambsquarters   --     0        0    0                                         Morningglory    0      0        0    0                                         Pigweed         0      0        0    0                                         Rape            0      0        0    0                                         Ryegrass        2      0        4    0                                         Sorghum         0      0        0    0                                         Soybean         0      0        0    0                                         Speedwell       0      0        0    --                                        Sugar beet      0      0        0    0                                         Velvetleaf      0      0        0    0                                         Wheat           0      0        0    0                                         Wild buckwheat  0      0        0    --                                        Wild oat        0      0        0    0                                         Barnyardgrass   10     10       10   9                                         Rice Japonica   5      2        8    8                                         Umbrella sedge  8      8        9    9                                         ______________________________________                                                       COMPOUND                                                         Rate (31 g/ha)  1      3        4    5                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      0        0    0                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        0    0                                         Chickweed       0      0        0    --                                        Corn            0      0        0    0                                         Cotton          0      0        0    0                                         Crabgrass       0      0        0    0                                         Downy brome     0      0        0    0                                         Duck salad      0      0        2    6                                         Giant foxtail   0      0        0    0                                         Lambsquarters   0      0        0    0                                         Morningglory    0      0        0    0                                         Pigweed         0      0        0    0                                         Rape            0      0        0    0                                         Ryegrass        0      0        0    0                                         Sorghum         0      0        0    0                                         Soybean         0      0        0    0                                         Speedwell       0      0        0    0                                         Sugar beet      0      0        0    0                                         Velvetleaf      0      0        0    0                                         Wheat           0      0        0    0                                         Wild buckwheat  0      0        0    --                                        Wild oat        0      0        0    0                                         Barnyardgrass   10     10       10   9                                         Rice Japonica   1      0        4    6                                         Umbrella sedge  8      7        8    9                                         ______________________________________                                                       COMPOUND                                                         Rate (16 g/ha)  1      3        4    5                                         ______________________________________                                         POSTEMERGENCE                                                                  Barley Igri     0      0        0    0                                         Bedstraw        0      0        0    --                                        Blackgrass      0      0        0    0                                         Chickweed       0      0        0    0                                         Corn            0      0        0    0                                         Cotton          0      0        0    0                                         Crabgrass       0      0        0    0                                         Downy brome     0      0        0    0                                         Duck salad      0      0        0    0                                         Giant foxtail   0      0        0    0                                         Lambsquarters   0      0        0    0                                         Morningglory    0      0        0    0                                         Pigweed         0      0        0    0                                         Rape            0      0        0    0                                         Ryegrass        0      0        0    0                                         Sorghum         0      0        0    0                                         Soybean         0      0        0    0                                         Speedwell       0      0        0    0                                         Sugar beet      0      0        0    0                                         Velvetleaf      0      0        0    0                                         Wheat           0      0        0    0                                         Wild buckwheat  0      0        0    --                                        Wild oat        0      0        0    0                                         Barnyardgrass   9      10       9    6                                         Rice Japonica   0      0        3    2                                         Umbrella sedge  5      5        8    8                                         ______________________________________                                                       COMPOUND                                                         Rate (250 g/ha) 1      3        4    5                                         ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     4      0        0    --                                        Bedstraw        0      8        8    0                                         Blackgrass      10     8        10   10                                        Chickweed       9      9        9    9                                         Corn            4      2        6    7                                         Cotton          0      1        0    0                                         Crabgrass       9      9        10   10                                        Downy brome     8      3        8    --                                        Duck salad      --     --       --   --                                        Giant foxtail   10     10       10   10                                        Lambsquarters   9      8        10   10                                        Morningglory    0      2        3    0                                         Pigweed         8      7        8    8                                         Rape            0      0        7    --                                        Ryegrass        10     --       10   10                                        Sorghum         4      2        4    2                                         Soybean         0      0        3    0                                         Speedwell       8      6        10   9                                         Sugar beet      5      0        3    0                                         Velvetleaf      8      8        9    8                                         Wheat           3      0        0    --                                        Wild buckwheat  4      6        6    7                                         Wild oat        4      5        8    9                                         Barnyardgrass   --     --       --   --                                        Rice Japonica   --     --       --   --                                        Umbrella sedge  --     --       ----                                           ______________________________________                                                       COMPOUND                                                         Rate (125 g/ha) 1      3        4    5                                         ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0      0        0    5                                         Bedstraw        0      3        8    --                                        Blackgrass      7      0        7    9                                         Chickweed       9      0        8    9                                         Corn            3      0        4    2                                         Cotton          0      0        0    0                                         Crabgrass       9      9        10   10                                        Downy brome     5      3        3    6                                         Duck salad      --     --       --   --                                        Giant foxtail   10     9        10   9                                         Lambsquarters   9      4        9    9                                         Morningglory    0      0        2    0                                         Pigweed         7      7        8    8                                         Rape            0      0        0    4                                         Ryegrass        8      5        9    8                                         Sorghum         2      0        3    0                                         Soybean         0      0        0    0                                         Speedwell       5      6        9    9                                         Sugar beet      5      0        0    --                                        Velvetleaf      7      8        8    7                                         Wheat           0      0        0    4                                         Wild buckwheat  --     6        0    0                                         Wild oat        2      0        3    7                                         Barnyardgrass   --     --       --   --                                        Rice Japonica   --     --       --   --                                        Umbrella sedge  --     --       --   --                                        ______________________________________                                                       COMPOUND                                                         Rate (62 g/ha)  1      3        4    5                                         ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0      0        0    0                                         Bedstraw        0      2        --   0                                         Blackgrass      5      0        0    5                                         Chickweed       8      0        8    5                                         Corn            0      0        0    0                                         Cotton          0      0        0    0                                         Crabgrass       9      8        10   9                                         Downy brome     3      2        0    0                                         Duck salad      --     --       --   --                                        Giant foxtail   10     9        9    8                                         Lambsquarters   4      3        9    8                                         Morningglory    0      0        0    0                                         Pigweed         6      2        7    7                                         Rape            0      --       0    3                                         Ryegrass        2      0        8    6                                         Sorghum         1      0        2    0                                         Soybean         0      0        0    0                                         Speedwell       0      5        9    6                                         Sugar beet      0      0        0    0                                         Velvetleaf      6      6        8    7                                         Wheat           0      0        0    3                                         Wild buckwheat  4      0        --   0                                         Wild oat        --     0        3    0                                         Barnyardgrass   --     --       --   --                                        Rice Japonica   --     --       --   --                                        Umbrella sedge  --     --       --   --                                        ______________________________________                                                       COMPOUND                                                          Rate (31 g/ha) 1      3        4    5                                         ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0      0        0    0                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        0    5                                         Chickweed       0      0        8    5                                         Corn            0      0        0    0                                         Cotton          0      0        0    0                                         Crabgrass       7      7        8    8                                         Downy brome     0      0        --   0                                         Duck salad      --     --       --   --                                        Giant foxtail   7      7        9    6                                         Lambsquarters   4      0        0    8                                         Morningglory    0      0        0    0                                         Pigweed         4      0        5    5                                         Rape            --     0        0    0                                         Ryegrass        0      0        3    0                                         Sorghum         1      0        0    0                                         Soybean         0      0        0    0                                         Speedwell       0      0        --   6                                         Sugar beet      0      0        --   0                                         Velvetleaf      5      5        6    5                                         Wheat           0      0        0    2                                         Wild buckwheat  4      0        --   0                                         Wild oat        0      0        0    0                                         Barnyardgrass   --     --       --   --                                        Rice Japonica   --     --       --   --                                        Umbrella sedge  --     --       --   --                                        ______________________________________                                                       COMPOUND                                                         Rate (16 g/ha)  1      3        4    5                                         ______________________________________                                         PREEMERGENCE                                                                   Barley Igri     0      0        0    0                                         Bedstraw        0      0        0    0                                         Blackgrass      0      0        0    4                                         Chickweed       0      0        6    5                                         Corn            0      0        0    0                                         Cotton          0      0        0    0                                         Crabgrass       6      5        5    4                                         Downy brome     0      0        0    0                                         Duck salad      --     --       --   --                                        Giant foxtail   3      7        5    5                                         Lambsquarters   0      0        0    0                                         Morningglory    0      0        0    0                                         Pigweed         0      0        0    2                                         Rape            0      0        0    0                                         Ryegrass        0      0        --   0                                         Sorghum         0      0        0    0                                         Soybean         0      0        0    0                                         Speedwell       0      0        5    0                                         Sugar beet      0      0        0    0                                         Velvetleaf      3      2        5    3                                         Wheat           0      0        0    0                                         Wild buckwheat  --     0        --   0                                         Wild oat        0      0        0    0                                         Barnyardgrass   --     --       --   --                                        Rice Japonica   --     --       --   --                                        Umbrella sedge  --     --       --   --                                        ______________________________________                                    

TEST C

Plastic pots were partially filled with silt loam soil. The soil was then saturated with water. Japonica rice (Oryza sativa) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) duck salad (Heteranthera limosa), umbrella sedge (Cyperus difformis), and tubers selected from arrowhead (Sagittaria spp.), waterchestnut (Eleocharis spp.), were planted into this soil. After planting, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table C, are reported on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE C                                                          ______________________________________                                                    COMPOUND                                                            Rate (125 g/ha)                                                                             1           3      4                                              ______________________________________                                         PADDY                                                                          Arrowhead    0           --     3                                              Barnyardgrass                                                                               10          10     10                                             Duck salad   10          10     10                                             Japonica rice                                                                               1           0      2                                              Umbrella sedge                                                                              9           9      10                                             Waterchestnut                                                                               3           5      5                                              ______________________________________                                                    COMPOUND                                                            Rate (64 g/ha)                                                                              1           3      4                                              ______________________________________                                         PADDY                                                                          Arrowhead    0           --     3                                              Barnyardgrass                                                                               8           10     9                                              Duck salad   10          10     10                                             Japonica rice                                                                               1           0      1                                              Umbrella sedge                                                                              9           9      9                                              Waterchestnut                                                                               3           4      3                                              ______________________________________                                                    COMPOUND                                                            Rate (32 g/ha)                                                                              1           3      4                                              ______________________________________                                         PADDY                                                                          Arrowhead    0           --     3                                              Barnyardgrass                                                                               10          7      9                                              Duck salad   10          10     10                                             Japonica rice                                                                               0           0      0                                              Umbrella sedge                                                                              9           9      9                                              Waterchestnut                                                                               1           0      3                                              ______________________________________                                                    COMPOUND                                                            Rate (16 g/ha)                                                                              1           3      4                                              ______________________________________                                         PADDY                                                                          Arrowhead    --          --     0                                              Barnyardgrass                                                                               7           5      7                                              Duck salad   9           10     10                                             Japonica rice                                                                               0           0      0                                              Umbrella sedge                                                                              9           9      9                                              Waterchestnut                                                                               0           0      2                                              ______________________________________                                                    COMPOUND                                                            Rate (8 g/ha)                                                                               1           3      4                                              ______________________________________                                         PADDY                                                                          Arrowhead    3           --     0                                              Barnyardgrass                                                                               3           3      0                                              Duck salad   0           0      0                                              Japonica rice                                                                               0           0      0                                              Umbrella sedge                                                                              6           0      5                                              Waterchestnut                                                                               0           0      0                                              ______________________________________                                    

TEST D

Plastic pots were partially filled with silt loam soil. The soil was then flooded with water, Japonica rice (Oryza sativa) sprouted seeds and 1.5 leaf transplants were planted in the soil. Seeds of barnyardgrass (Echinochloa crus-galli) were planted in saturated soil and plants grown to the 2 and 3 leaf stages for testing. At testing, the water level for all plantings was raised to 2 cm above the soil surface. Chemical treatments were formulated in a non-phytotoxic solvent and applied directly to the paddy water. Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D are reported on a to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                  TABLE D                                                          ______________________________________                                                       COMPOUND                                                         Rate (250 g/ha)                                                                              1                                                                ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              10                                                               3-lf B.Y. Grass                                                                              10                                                               Jap Direct Seed                                                                              10                                                               Jap Rice Eff  6                                                                ______________________________________                                                     COMPOUND                                                           Rate (125 g/ha)                                                                              1           3      4                                             ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              10          9      10                                            3-lb B.Y. Grass                                                                              10          10     9                                             Jap Direct Seed                                                                              10          9      10                                            Jap Rice Eff  3           0      2                                             ______________________________________                                                     COMPOUND                                                           Rate (64 g/ha)                                                                               1           3      4                                             ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              10          10     9                                             3-lb B.Y. Grass                                                                              9           8      9                                             Jap Direct Seed                                                                              8           9      10                                            Jap Rice Eff  3           0      1                                             ______________________________________                                                     COMPOUND                                                           Rate (32 g/ha)                                                                               1           3      4                                             ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              10          8      9                                             3-lb B.Y. Grass                                                                              7           6      6                                             Jap Direct Seed                                                                              7           5      9                                             Jap Rice Eff  1           0      1                                             ______________________________________                                                     COMPOUND                                                           Rate (16 g/ha)                                                                               1           3      4                                             ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              8           6      6                                             3-lb B.Y. Grass                                                                              6           2      3                                             Jap Direct Seed                                                                              5           3      2                                             Jap Rice Eff  1           0      0                                             ______________________________________                                                     COMPOUND                                                           Rate (8 g/ha) 1           3      4                                             ______________________________________                                         PADDY                                                                          2-LF B.Y. Grass                                                                              5           3      2                                             3-lb B.Y. Grass                                                                              0           0      2                                             Jap Direct Seed                                                                              1           0      2                                             Jap Rice Eff  1           0      0                                             ______________________________________                                     

What is claimed is:
 1. A compound and stereoisomers of the following formula ##STR19## wherein m is 1,R¹ is straight chain C₁ -C₃ alkyl; R² is H, R³ and R⁴ are H, R⁵ and R⁶ are H, Q is CH₂ W or ##STR20## q and r are independently 0, 1 or 2; R⁷ is H, halogen, C₁ -C₃ alkyl, OR⁸, SR⁸ or CN; R⁸ is C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; Z is CH₂, NR⁹, O, S or may be CH and taken to form a double bond with an adjacent carbon; R⁹ is H or C₁ -C₃ alkyl; W is phenyl optionally substituted with 1-3 substituents selected from halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, OH, CN, C₁ -C₃ haloalkyl, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₂ -C₄ alkenyl and C₂ -C₄ alkynyl; or W is selected from the group consisting of tetrahydropyran, furan, tetrahydrofuran, thiophene and pyridine, said heterocyclic ring optionally substituted with 1-2 substituents selected from the group consisting of halogen, CH₃ and OCH₃ ;provided that 1) the sum of q and r is 0-2; and 2if the sum of q and r is 0 then Z is CH₂.
 2. The compounds of claim 1 wherein:Q is CH₂ W or ##STR21## W is phenyl optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃ ; or W is tetrahydroyran, tetrahdrofuran, thiophene, pyridine or each ring optionally substituted with 1-2 substituents selected from F, Cl, Br, CH₃ and OCH₃.
 3. The compounds of claim 2 wherein:Q is CH₂ W, Q-1, Q-3, Q-4, Q-6, Q-7, Q-8 or Q-15; W is phenyl optionally substituted with 1-2 substituents selected from F, Cl, Br and CH₃ ; tetrahydrofuran; thiophene optionally substituted with Cl or Br; or pyridine.
 4. The compounds of claim 3 wherein:R¹ is CH₃ or CH₂ CH₃ ; Q is CH₂ W.
 5. The compound of claim 3 which is (1α,2α,4α,5β,6α)-(+/-)-5-[(2-fluorophenyl)-methoxy]-6-methyl-7-oxatricyclo[4.2.1.0²,4 ]-nonane.
 6. An agriculturally suitable composition for controlling the growth o f undesired vegetation comprising an effective amount of a compound of any one of claims 1-5 and at least one of the following: surfactant, solid or liquid diluent. 